IL231694A - Process for producing nitrile compound - Google Patents

Description

S34816 (Document Name) Specification (Title of the Invention) Process for producing nitrile compound (Technical Field) (0001) The present invention relates to a process for producing a nitrile compound.

(Background Art) (0002) Patent document 1 describes that a nitrile compound represented by formula (4) : wherein R1 represents an alkyl group having 1 to 6 carbon atoms and optionally having a halogen atom, and R2 represents an alkyl group having 1 to 6 carbon atoms, is useful for harmful insects and harmful arthropods.

Patent document 1 describes a process for producing a nitrile compound represented by formula (4) comprising reacting a compound represented by formula (1) : wherein R1 is as defined above, and 1 , 4-cyclohexanedione monoethylene acetal, reducing the S34816 generated olefin compound, and then, converting an ethylene acetal portion of the product into a methoxyimino group. (Prior Technological Document) (Patent Document) (0003) (Patent document 1) JP-A No. 2009-256302 (Summary of the Invention) (Problem to be Solved by the Invention) (0004) The process described in patent document 1 is a process using a compound represented by formula (1) as a starting substance and containing at least four steps, thus, is not necessarily industrially satisfactory process from the standpoint of the number of steps.

(Means for Solving the Problem) (0005) The present invention is as described below. [1] A process for producing a nitrile compound represented by formula (4) : wherein R and R are as defined below, the process comprising: reacting together a compound represented by formula (1) : S34816 wherein R1 represents an alkyl group having 1 to 6 carbon atoms and optionally having a halogen atom, a compound represented by formula (2) : wherein represents an alkyl group having 1 to 6 carbon atoms, and a compound represented by formula (3) : wherein R3 , R4 and R5 each independently represents an alkyl group having 1 to 20 carbon atoms, R6 represents an alkyl group having 1 to 20 carbon atoms or a benzyl group optionally having a substituent, and R7 each independently represents an alkyl group having 1 to 20 carbon atoms. [2] The process according to [1], wherein R6 is an alkyl group having 1 to 20 carbon atoms or a benzyl group. [3] The process according to [1] or [2], the process further comprising: reacting a compound represented by formula (5) : S34816 wherein R3 , R4 , R5 and R6 are as defined above, and X~ represents a monovalent anion except for a hydroxide ion and an alkoxide ion, with a compound represented by formula (6) : wherein R is as defined above, and M represents an alkali metal ion, to give the compound represented by formula (3) . [4] The process according to [1] or [2], the process further comprising: reacting a compound represented by formula (5) : wherein R3 , R4 , R5 and R6 are as defined above, and X~ represents a monovalent anion except for hydroxide ion and an alkoxide ion, a compound represented by formula (7) : S34816 ® 0 m M BH4 (7) wherein M+ represents an alkali metal ion, and a compound represented by formula (8) : wherein R is as defined above, to give the compound represented by formula (3) . [5] The process according to [4], wherein the compound represented by formula (5), the compound represented by formula (7) and the compound represented by formula (8) are reacted in a non-aqueous system. [6] The process according to [1] or [2], the process further comprising: reacting a compound represented by formula (5) : wherein R3 , R4 , R5 and R6 are as defined above, and X represents a monovalent anion except for a hydroxide and an alkoxide ion, with a compound represented by formula (7) : © © m M BH4 (' ) wherein M represents an alkali metal ion, S34816 mixing the resultant mixture with a compound by formula wherein R7 is as defined above, to give the compound represented by formula [7] The process according to [1] or [2] further comprising: reacting a compound represented by formula M ® B0H4 m(7) wherein M+ represents an alkali metal ion, with a compound represented by formula (8) : wherein R7 is as defined above, to give a compound represented by formula (6) : wherein R7 is as defined above, and M+ represents an alkali metal ion, and reacting the resultant compound represented by formula (6) S34816 with a compound represented by formula (5) : wherein R3 , R4 , R5 and R6 are as defined above, and X~ represents a monovalent anion except for a hydroxide ion and an alkoxide ion, to give the compound represented by formula (3) .

(Effect of the Invention) (0006) According to the present invention, a nitrile compound represented by formula (4) can be produced from a compound represented by formula (1) in a fewer steps.

(Mode for Carrying Out the Invention) (0007) The alkyl group having 1 to 6 carbon atoms represented by R1 includes a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, a pentyl group, a neopentyl group, a hexyl group and the like, preferably alkyl groups having 1 to 4 carbon atoms, more preferably a methyl group. The alkyl group may optionally S34816 have a halogen atom.

R1 is preferably an alkyl group having 1 to 6 carbon atoms and having a halogen atom.

The halogen atom includes a fluorine atom, a chlorine atom, a bromine atom, an iodine atom and the like, preferably a fluorine atom. (0008) The alkyl group having 1 to 6 carbon atoms and having a halogen atom includes alkyl groups having 1 to 6 carbon atoms and having a fluorine atom such as a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a 1 , 1 , 2 , 2 , 2-pentafluoroethyl group, a 2 , 2 , 2-trifluoroethyl group, a 1 , 1-difluoroethyl group, a 1,1,2,2,3,3,3-heptafluoropropyl group, a 1 , 1-difluoropropyl group, a 2,2-difluoropropyl group, a 3 , 3 , 3-trifluoropropyl group, a 1 , 1 , 2 , 2 , 3 , 3 , 4 , 4 , 4-nonafluorobutyl group, a 1,1-difluorobutyl group, a 2 , 2-difluorobutyl group, a 1 , 1 , 2 , 2 , 3 , 3 , 4 , 4 , 5 , 5 , 5-undecafluoropentyl group, a 3 , 3 , 4 , 4 , 4-pentafluoropropyl group, a 3- (trifluoromethyl ) -3 , 4 , 4 , 4-pentafluorobutyl group, a 3,3,4,4,5,5,6,6,6-nonafluorohexyl group, a 1 , 1-difluoropentyl group and a 2 , 2-difluoropentyl group; alkyl groups having 1 to 6 carbon atoms and having a chlorine atom such as a chloromethyl group, a dichloromethyl group, a trichloromethyl group, a 1,1,2,2,2- S34816 pentachloroethyl group, a 2 , 2 , 2-trichloroethyl group, a 1 , 1-dichloroethyl group, a 1 , 1 , 2 , 2 , 3 , 3 , 3-heptachloropropyl group, a 1 , 1-dichloropropyl group, a 2 , 2-dichloropropyl group, a 3 , 3 , 3-trichloropropyl group, a 1,1,2,2,3,3,4,4,4-nonachlorobutyl group, a 1 , 1-dichlorobutyl group, a 2,2-dichlorobutyl group, a 1,1,2,2,3,3,4,4,5,5,5-undecachloropentyl group, a 3 , 3 , 4 , 4 , 4-pentachloropropyl group, a 3- ( trichloromethyl ) -3 , 4 , 4 , 4-pentachlorobutyl group, a 3 , 3 , 4 , 4 , 5 , 5 , 6 , 6 , 6-nonachlorohexyl group, a 1,1-dichloropentyl group and a 2 , 2-dichloropentyl group; alkyl groups having 1 to 6 carbon atoms and having a bromine atom such as a bromomethyl group, a dibromomethyl group, a tribromomethyl group, a 1 , 1 , 2 , 2 , 2-pentabromoethyl group, a 2 , 2 , 2-tribromoethyl group, a 1 , 1-dibromoethyl group, a 1 , 1 , 2 , 2 , 3 , 3 , 3-heptabromopropyl group, a 1,1-dibromopropyl group, a 2 , 2-dibromopropyl group, a 3,3,3-tribromopropyl group, a 1 , 1 , 2 , 2 , 3 , 3 , 4 , 4 , 4-nonabromobutyl group, a 1 , 1-dibromobutyl group, a 2 , 2-dibromobutyl group, a 1 , 1 , 2 , 2 , 3 , 3 , 4 , 4 , 5 , 5 , 5-undecabromopentyl group, a 3 , 3 , 4 , 4 , 4-pentabromopropyl group, a 3- (tribromomethyl ) -3 , 4 , 4 , 4-pentabromobutyl group, a 3,3,4,4,5,5,6,6,6-nonabromohexyl group, a 1 , 1-dibromopentyl group and a 2,2-dibromopentyl group; alkyl groups having 1 to 6 carbon atoms and having an iodine atom such as an iodomethyl group, a diiodomethyl S34816 group, a triiodomethyl group, a 1 , 1 , 2 , 2 , 2-pentaiodoethyl group, a 2 , 2 , 2-triiodoethyl group, a 1 , 1-diiodoethyl group, a 1 , 1 , 2 , 2 , 3 , 3 , 3-heptaiodopropyl group, a 1 , 1-diiodopropyl group, a 2 , 2-diiodopropyl group, a 3 , 3 , 3-triiodopropyl group, a 1 , 1 , 2 , 2 , 3 , 3 , 4 , 4 , 4-nonaiodobutyl group, a 1,1-diiodobutyl group, a 2 , 2-diiodobutyl group, a 1 , 1 , 2 , 2 , 3 , 3 , 4 , 4 , 5 , 5 , 5-undecaiodopentyl group, a 3,3,4,4,4-pentaiodopropyl group, a 3- (triiodomethyl ) -3 , 4 , 4 , 4-pentaiodobutyl group, a 3 , 3 , 4 , 4 , 5 , 5 , 6 , 6 , 6-nonaiodohexyl group, a 1 , 1-diiodopentyl group and a 2 , 2-diiodopentyl group ; (0009) alkyl groups having 1 to 6 carbon atoms and having a fluorine atom and a chlorine atom such as a chlorodifluoromethyl group, a 1 , 2-dichloro-l , 2 , 2-trifluoroethyl group, a 1 , l-dichloro-2 , 2 , 2-trifluoroethyl group, a 1-chloro-l , 3 , 3 , 3-tetrafluoropropyl group, a 2,3-dichloro-2 , 3 , 3-trifluoropropyl group and a 2 , 2-dichloro- 3 , 3 , 3-trifluoropropyl group; alkyl groups having 1 to 6 carbon atoms and having a fluorine atom and a bromine atom such as a 2,2-dibromo-3 , 3 , 3-trifluoropropyl group, a 2-bromo-3 , 3 , 3-trifluoropropyl group, a 2 , 3-dibromo-3 , 3-difluoropropyl group, a 3-bromo-3 , 3-difluoropropyl group, a 1-bromo-1 , 3 , 3 , 3-tetrafluoropropyl group, a l-bromo-2 , 2 , 3 , 3 , 3- S34816 pentafluoropropyl group, a 1 , 3-dibromo-2 , 2 , 3 , 3-tetrafluoropropyl group, a 3-bromo-2 , 3 , 3-trifluoropropyl group, a 3-bromo-2 , 2 , 3 , 3-tetrafluoropropyl group, a 2,3-dibromo-2 , 3 , 3-trifluoropropyl group and a 3-bromo-3 , 3-difluoropropyl group; alkyl groups having 1 to 6 carbon atoms and having a fluorine atom and an iodine atom such as a 2,2-diiodo-3 , 3 , 3-trifluoropropyl group, a 2-iodo-3 , 3 , 3-trifluoropropyl group, a 2 , 3-diiodo-3 , 3-difluoropropyl group, a 3-iodo-3,3-difluoropropyl group, a 1-iodo-l , 3 , 3 , 3-tetrafluoropropyl group, a l-iodo-2 , 2 , 3 , 3 , 3-pentafluoropropyl group, a 1,3-diiodo-2 , 2 , 3 , 3-tetrafluoropropyl group, a 3-iodo-2 , 3 , 3-trifluoropropyl group, a 3-iodo-2 , 2 , 3 , 3-tetrafluoropropyl group, a 2 , 3-diiodo-2 , 3 , 3-trifluoropropyl group and a 3-iodo-3 , 3-difluoropropyl group; alkyl groups having 1 to 6 carbon atoms and having a chlorine atom and a bromine atom such as a 2,2-dibromo-3 , 3 , 3-trichloropropyl group, a 2-bromo-3 , 3 , 3-trichloropropyl group, a 2 , 3-dibromo-3 , 3-dichloropropyl group, a 3-bromo-3 , 3-dichloropropyl group, a 1-bromo-1 , 3 , 3 , 3-tetrachloropropyl group, a l-bromo-2 , 2 , 3 , 3 , 3-pentachloropropyl group, a 1 , 3-dibromo-2 , 2 , 3 , 3-tetrachloropropyl group, a 3-bromo-2 , 3 , 3-trichloropropyl group, a 3-bromo-2 , 2 , 3 , 3-tetrachloropropyl group, a 2,3-dibromo-2 , 3 , 3-trichloropropyl group and a 3-bromo-3,3- S34816 dichloropropyl group; etc. The alkyl group having 1 to 6 carbon atoms and having a halogen atom is preferably an alkyl group having 1 to 6 carbon atoms and having one kind of halogen atom, more preferably an alkyl group having 1 to 6 carbon atoms and having a fluorine atom. (0010) The compound (1) can be obtained, for example, by a method described in patent document 1.

The compound (1) includes methylsulfonylacetonitrile , ethylsulfonylacetonitrile , propylsulfonylacetonitrile ;: fluoromethylsulfonylacetonitrile , difluoromethy1sulfonylacetonitrile , trifluoromethylsulfonylacetonitrile , 1,1,2,2,2-pentafluoroethylsulfonylacetonitrile , 2,2,2-trifluoroethylsulfonylacetonitrile , 1, 1-difluoroethylsulfonylacetonitrile , 1,1,2,2,3,3,3-heptafluoropropylsulfonylacetonitrile , 1, 1-difluoropropylsulfonylacetonitrile , 2, 2-difluoropropylsulfonylacetonitrile , 3,3,3-trifluoropropylsulfonylacetonitrile , 1,1,2,2,3,3,4,4,4-nonafluorobutylsulfonylacetonitrile , 1, 1-difluorobutylsulfonylacetonitrile , 2, 2-difluorobutylsulfonylacetonitrile , 1,1,2,2,3,3,4,4,5,5,5-undecafluoropentylsulfonylacetonitrile , 3,3,4,4,4-pentafluoropropylsulfonylacetonitrile , 3- ( trifluoromethyl ) - S34816 3,4,4, 4-pentafluorobutylsulfonylacetonitrile, 3,3,4,4,5,5,6,6, 6-nonafluorohexylsulfonylacetonitrile , 1,1-difluoropentylsulfonylacetonitrile , 2, 2-difluoropentylsulfonylacetonitrile ; chloromethylsulfonylacetonitrile , dichloromethylsulfonylacetonitrile , trichloromethylsulfonylacetonitrile , 1,1,2,2,2-pentachloroethylsulfonylacetonitrile , 2,2,2-trichloroethylsulfonylacetonitrile , 1, 1-dichloroethylsulfonylacetonitrile , 1,1,2,2,3,3,3-heptachloropropylsulfonylacetonitrile , 1, 1-dichloropropylsulfonylacetonitrile , 2, 2-dichloropropylsulfonylacetonitrile , 3,3,3-trichloropropylsulfonylacetonitrile ; chlorodifluoromethylsulfonylacetonitrile , 1, 2-dichlorol, 2, 2-trifluoroethylsulfonylacetonitrile , 1, 1-dichloro-2, 2, 2-trifluoroethylsulfonylacetonitrile , 1-chloro-1, 3, 3, 3-tetrafluoropropylsulfonylacetonitrile , 2, 3-dichloro-2 , 3 , 3-trifluoropropylsulfonylacetonitrile and 2,2-dichloro-3 , 3 , 3-trifluoropropylsulfonylacetonitrile , and the like. (0011) The alkyl group having 1 to 6 carbon atoms represented S34816 by R includes the same groups as the alkyl group having 1 to 6 carbon atoms represented by R1 , preferably alkyl groups having 1 to 4 carbon atoms, more preferably a methyl group . (0012) The compound (2) can be obtained, for example, by a method described in Vogel, Cresswell, Jeffery. and Leicester: J. Chem. Soc. 1952. 514-549.

The compound (2) includes 1 , 4-cyclohexanedione monomethyloxime ether, 1 , 4-cyclohexanedione monoethyloxime ether, 1 , 4-cyclohexanedione monopropyloxime ether, 1,4-cyclohexanedione monoisopropyloxime ether, 1,4-cyclohexanedione monobutyloxime ether, 1 , 4-cyclohexanedione monosec-butyloxime ether, 1 , 4-cyclohexanedione monotert-butyloxime ether, 1 , 4-cyclohexanedione monopentyloxime ether, 1 , 4-cyclohexanedione mononeopentyloxime ether, 1,4-cyclohexanedione monohexyloxime ether and the like. (0013) The alkyl group having 1 to 20 carbon atoms represented by R3 , R4 and R5 includes a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, a pentyl group, a neopentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, a dodecyl group, a tridecyl group, a tetradecyl group, a pentadecyl group, a hexadecyl group, a heptadecyl group, an octadecyl group, a nonadecyl group, an icosyl group and the like, preferably alkyl groups having 1 to 12 carbon atoms, more preferably alkyl groups having 1 to 6 carbon atoms.

All of R3 , R4 and R5 are preferably the same group. (0014) The alkyl group having 1 to 20 carbon atoms represented by R6 includes the same groups as the alkyl group having 1 to 20 carbon atoms represented by R3 , R4 and R5.

The substituent on a benzyl group includes a halogen atom, an alkyl group optionally having a halogen atom, an alkoxy group, an alkylamino group, an alkylthio group, an alkylsulfonyl group and a cyano group.

The halogen atom includes the same atoms as the halogen atom exemplified for R1.

The alkyl group optionally having a halogen atom includes the same groups as the alkyl group having 1 to 6 carbon atoms and the alkyl group having 1 to 6 carbon atoms and having a halogen atom represented by R1.

The alkoxy group includes alkoxy groups having 1 to 4 carbon atoms such as a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butyloxy group, a sec-butyloxy group, an isobutyloxy group and a tert-butyloxy group.

The alkylamino group includes alkylamino groups having 1 to 4 carbon atoms such as a methylamino group, a dimethylamino group, an ethylamino group and a diethylamino group .

The alkylthio group includes alkylthio groups having 1 to 4 carbon atoms such as a methylthio group, an ethylthio group and a propylthio group.

The alkylsulfonyl group includes alkylsulfonyl groups having 1 to 4 carbon atoms such as a methanesulfonyl group, an ethanesulfonyl group and a propanesulfonyl group.

R6 is preferably an alkyl group having 1 to 12 carbon atoms or a benzyl group, more preferably an alkyl group having 1 to 6 carbon atoms or a benzyl group, further preferably a methyl group or a benzyl group, particularly preferably a benzyl group. (0015) The alkyl group having 1 to 20 carbon atoms represented by R7 includes the same groups as the alkyl group having 1 to 20 carbon atoms represented by R3 , R4 and R5 , preferably alkyl groups having 1 to 12 carbon atoms, more preferably alkyl groups having 1 to 6 carbon atoms. All of R7 are preferably the same group. (0016) The compound (3) is preferably a compound (3) in which R7 is a methyl group, more preferably a compound (3) in which R7 is a methyl group and R3 , R4 and R5 each independently represents an alkyl group having 1 to 6 carbon atoms, further preferably a compound (3) in which R7 is methyl group and all of R3 , R4 and R5 are the same alkyl group having 1 to 6 carbon atoms, particularly preferably a compound (3) in which R7 is a methyl group, all of R3 , R4 and R5 are the same alkyl group having 1 to 6 carbon atoms and R6 is a benzyl group. (0017) The compound (3) includes triacetoxyborohydride compounds such as tetramethylammonium triacetoxyborohydride , tetraethylammonium triacetoxyborohydride , tetrapropylammonium triacetoxyborohydride , tetrabutylammonium triacetoxyborohydride , tetraisobutylammonium triacetoxyborohydride , tetrapentylammonium triacetoxyborohydride , tetrahexylammonium triacetoxyborohydride , ethyItrimethylammonium triacetoxyborohydride , propyltrimethylammonium triacetoxyborohydride , butyltrimethylammonium triacetoxyborohydride , pentyltrimethylammonium triacetoxyborohydride , S34816 hexyltrimethylammonium triacetoxyborohydride , benzyltrimethylammonium triacetoxyborohydride , methyltriethylammonium triacetoxyborohydride , propyltriethylammonium triacetoxyborohydride , butyltriethylammonium triacetoxyborohydride , pentyltriethylammonium triacetoxyborohydride , hexyltriethylammonium triacetoxyborohydride , benzyltriethylammonium triacetoxyborohydride , methyltripropylammonium triacetoxyborohydride , ethyltripropylammonium triacetoxyborohydride , butyltripropylammonium triacetoxyborohydride , pentyltripropylammonium triacetoxyborohydride , hexyltripropylammonium triacetoxyborohydride , benzyltripropylammonium triacetoxyborohydride , methyltributylammonium triacetoxyborohydride , ethyltributylammonium triacetoxyborohydride , propyltributylammonium triacetoxyborohydride , pentyltributylammonium triacetoxyborohydride , hexyltributylammonium triacetoxyborohydride , benzyltributylammonium triacetoxyborohydride , methyltripentylammonium triacetoxyborohydride , ethyltripentylammonium triacetoxyborohydride , propyltripentylammonium triacetoxyborohydride , butyltripentylammonium triacetoxyborohydride , hexyltripentylammonium triacetoxyborohydride , S34816 benzyltripentylammonium triacetoxyborohydride , methyltrihexylammonium triacetoxyborohydride , ethyltrihexylammonium triacetoxyborohydride , propyltrihexylammonium triacetoxyborohydride , butyltrihexylammonium triacetoxyborohydride , pentyltrihexylammonium triacetoxyborohydride and benzyltrihexylammonium triacetoxyborohydride ; (0018) tripropionyloxyborohydride compounds such as tetramethylammonium tripropionyloxyborohydride , tetraethylammonium tripropionyloxyborohydride , tetrapropylammonium tripropionyloxyborohydride , tetrabutylammonium tripropionyloxyborohydride , tetraisobutylammonium tripropionyloxyborohydride , tetrapentylammonium tripropionyloxyborohydride , tetrahexylammonium tripropionyloxyborohydride , tetrahexylammonium tripropionyloxyborohydride , ethyItrimethylammonium tripropionyloxyborohydride , propyltrimethylammonium tripropionyloxyborohydride , butyltrimethylammonium tripropionyloxyborohydride , pentyltrimethylammonium tripropionyloxyborohydride , hexyltrimethylammonium tripropionyloxyborohydride , benzyltrimethylammonium tripropionyloxyborohydride , methyltriethylammonium tripropionyloxyborohydride , propyltriethylammonium tripropionyloxyborohydride , S34816 butyltriethylammonium tripropionyloxyborohydride , pentyltriethylammonium tripropionyloxyborohydride , hexyltriethylammonium tripropionyloxyborohydride , benzyltriethylammonium tripropionyloxyborohydride , methyltripropylammonium tripropionyloxyborohydride , ethyltripropylammonium tripropionyloxyborohydride , butyltripropylammonium tripropionyloxyborohydride , pentyltripropylammonium tripropionyloxyborohydride , hexyltripropylammonium tripropionyloxyborohydride , benzyltripropylammonium tripropionyloxyborohydride , methyltributylammonium tripropionyloxyborohydride , ethyltributylammonium tripropionyloxyborohydride , propyltributylammonium tripropionyloxyborohydride , pentyltributylammonium tripropionyloxyborohydride , hexyltributylammonium tripropionyloxyborohydride , benzyltributylammonium tripropionyloxyborohydride , methyltripentylammonium tripropionyloxyborohydride , ethyltripentylammonium tripropionyloxyborohydride , propyltripentylammonium tripropionyloxyborohydride , butyltripentylammonium tripropionyloxyborohydride , hexyltripentylammonium tripropionyloxyborohydride , benzyltripentylammonium tripropionyloxyborohydride , methyltrihexylammonium tripropionyloxyborohydride , ethyltrihexylammonium tripropionyloxyborohydride , propyltrihexylammonium tripropionyloxyborohydride , S34816 butyltrihexylammonium tripropionyloxyborohydride , pentyltrihexylammonium tripropionyloxyborohydride and benzyltrihexylammonium tripropionyloxyborohydride ; (0019) tributanoyloxyborohydride compounds such as tetramethylammonium tributanoyloxyborohydride , tetraethylammonium tributanoyloxyborohydride , tetrapropylammonium tributanoyloxyborohydride , tetrabutylammonium tributanoyloxyborohydride , tetraisobutylammonium tributanoyloxyborohydride , tetrapentylammonium tributanoyloxyborohydride , tetrahexylammonium tributanoyloxyborohydride , tetrahexylammonium tributanoyloxyborohydride , ethyItrimethylammonium tributanoyloxyborohydride , propyltrimethylammonium tributanoyloxyborohydride , butyltrimethylammonium tributanoyloxyborohydride , pentyltrimethylammonium tributanoyloxyborohydride , hexyltrimethylammonium tributanoyloxyborohydride , benzyltrimethylammonium tributanoyloxyborohydride , methyltriethylammonium tributanoyloxyborohydride , propyltriethylammonium tributanoyloxyborohydride , butyltriethylammonium tributanoyloxyborohydride , pentyltriethylammonium tributanoyloxyborohydride , hexyltriethylammonium tributanoyloxyborohydride , benzyltriethylammonium tributanoyloxyborohydride , S34816 methyltripropylammonium tributanoyloxyborohydride , ethyltripropylammonium tributanoyloxyborohydride , butyltripropylammonium tributanoyloxyborohydride , pentyltripropylammonium tributanoyloxyborohydride , hexyltripropylammonium tributanoyloxyborohydride , benzyltripropylammonium tributanoyloxyborohydride , methyltributylammonium tributanoyloxyborohydride , ethyltributylammonium tributanoyloxyborohydride , propyltributylammonium tributanoyloxyborohydride , pentyltributylammonium tributanoyloxyborohydride , hexyltributylammonium tributanoyloxyborohydride , benzyltributylammonium tributanoyloxyborohydride , methyltripentylammonium tributanoyloxyborohydride , ethyltripentylammonium tributanoyloxyborohydride , propyltripentylammonium tributanoyloxyborohydride , butyltripentylammonium tributanoyloxyborohydride , hexyltripentylammonium tributanoyloxyborohydride , benzyltripentylammonium tributanoyloxyborohydride , methyltrihexylammonium tributanoyloxyborohydride , ethyltrihexylammonium tributanoyloxyborohydride , propyltrihexylammonium tributanoyloxyborohydride , butyltrihexylammonium tributanoyloxyborohydride , pentyltrihexylammonium tributanoyloxyborohydride and benzyltrihexylammonium tributanoyloxyborohydride ; (0020) S34816 tripentanoyloxyborohydride compounds such as tetramethylammonium tripentanoyloxyborohydride , tetraethylammonium tripentanoyloxyborohydride , tetrapropylammonium tripentanoyloxyborohydride , tetrabutylammonium tripentanoyloxyborohydride , tetraisobutylammonium tripentanoyloxyborohydride , tetrapentylammonium tripentanoyloxyborohydride , tetrahexylammonium tripentanoyloxyborohydride , tetrahexylammonium tripentanoyloxyborohydride , ethyItrimethylammonium tripentanoyloxyborohydride , propyltrimethylammonium tripentanoyloxyborohydride , butyltrimethylammonium tripentanoyloxyborohydride , pentyltrimethylammonium tripentanoyloxyborohydride , hexyltrimethylammonium tripentanoyloxyborohydride , benzyltrimethylammonium tripentanoyloxyborohydride , methyltriethylammonium tripentanoyloxyborohydride , propyltriethylammonium tripentanoyloxyborohydride , butyltriethylammonium tripentanoyloxyborohydride , pentyltriethylammonium tripentanoyloxyborohydride , hexyltriethylammonium tripentanoyloxyborohydride , benzyltriethylammonium tripentanoyloxyborohydride , methyltripropylammonium tripentanoyloxyborohydride , ethyltripropylammonium tripentanoyloxyborohydride , butyltripropylammonium tripentanoyloxyborohydride , pentyltripropylammonium tripentanoyloxyborohydride , S34816 hexyltripropylammonium tripentanoyloxyborohydride , benzyltripropylammonium tripentanoyloxyborohydride , methyltributylammonium tripentanoyloxyborohydride , ethyltributylammonium tripentanoyloxyborohydride , propyltributylammonium tripentanoyloxyborohydride , pentyltributylammonium tripentanoyloxyborohydride , hexyltributylammonium tripentanoyloxyborohydride , benzyltributylammonium tripentanoyloxyborohydride , methyltripentylammonium tripentanoyloxyborohydride , ethyltripentylammonium tripentanoyloxyborohydride , propyltripentylammonium tripentanoyloxyborohydride , butyltripentylammonium tripentanoyloxyborohydride , hexyltripentylammonium tripentanoyloxyborohydride , benzyltripentylammonium tripentanoyloxyborohydride , methyltrihexylammonium tripentanoyloxyborohydride , ethyltrihexylammonium tripentanoyloxyborohydride , propyltrihexylammonium tripentanoyloxyborohydride , butyltrihexylammonium tripentanoyloxyborohydride , pentyltrihexylammonium tripentanoyloxyborohydride and benzyltrihexylammonium tripentanoyloxyborohydride ; (0021) trihexanoyloxyborohydride compounds such as tetramethylammonium trihexanoyloxyborohydride , tetraethylammonium trihexanoyloxyborohydride , tetrapropylammonium trihexanoyloxyborohydride , S34816 tetrabutylammonium trihexanoyloxyborohydride , tetraisobutylammonium trihexanoyloxyborohydride , tetrapentylammonium trihexanoyloxyborohydride , tetrahexylammonium trihexanoyloxyborohydride , tetrahexylammonium trihexanoyloxyborohydride , ethyltrimethylammonium trihexanoyloxyborohydride , propyltrimethylammonium trihexanoyloxyborohydride , butyltrimethylammonium trihexanoyloxyborohydride , pentyltrimethylammonium trihexanoyloxyborohydride , hexyltrimethylammonium trihexanoyloxyborohydride , benzyltrimethylammonium trihexanoyloxyborohydride , methyltriethylammonium trihexanoyloxyborohydride , propyltriethylammonium trihexanoyloxyborohydride , butyltriethylammonium trihexanoyloxyborohydride , pentyltriethylammonium trihexanoyloxyborohydride , hexyltriethylammonium trihexanoyloxyborohydride , benzyltriethylammonium trihexanoyloxyborohydride , methyltripropylammonium trihexanoyloxyborohydride , ethyltripropylammonium trihexanoyloxyborohydride , butyltripropylammonium trihexanoyloxyborohydride , pentyltripropylammonium trihexanoyloxyborohydride , hexyltripropylammonium trihexanoyloxyborohydride , benzyltripropylammonium trihexanoyloxyborohydride , methyltributylammonium trihexanoyloxyborohydride , ethyltributylammonium trihexanoyloxyborohydride , S34816 propyltributylammonium trihexanoyloxyborohydride , pentyltributylammonium trihexanoyloxyborohydride , hexyltributylammonium trihexanoyloxyborohydride , benzyltributylammonium trihexanoyloxyborohydride , methyltripentylammonium trihexanoyloxyborohydride , ethyltripentylammonium trihexanoyloxyborohydride , propyltripentylammonium trihexanoyloxyborohydride , butyltripentylammonium trihexanoyloxyborohydride , hexyltripentylammonium trihexanoyloxyborohydride , benzyltripentylammonium trihexanoyloxyborohydride , methyltrihexylammonium trihexanoyloxyborohydride , ethyltrihexylammonium trihexanoyloxyborohydride , propyltrihexylammonium trihexanoyloxyborohydride , butyltrihexylammonium trihexanoyloxyborohydride , pentyltrihexylammonium trihexanoyloxyborohydride and benzyltrihexylammonium trihexanoyloxyborohydride ; (0022) triheptanoyloxyborohydride compounds such as tetramethylammonium triheptanoyloxyborohydride , tetraethylammonium triheptanoyloxyborohydride , tetrapropylammonium triheptanoyloxyborohydride , tetrabutylammonium triheptanoyloxyborohydride , tetraisobutylammonium triheptanoyloxyborohydride , tetrapentylammonium triheptanoyloxyborohydride , tetrahexylammonium triheptanoyloxyborohydride , S34816 tetrahexylammonium triheptanoyloxyborohydride , ethyItrimethylammonium triheptanoyloxyborohydride , propyltrimethylammonium triheptanoyloxyborohydride , butyltrimethylammonium triheptanoyloxyborohydride , pentyltrimethylammonium triheptanoyloxyborohydride , hexyltrimethylammonium triheptanoyloxyborohydride , benzyltrimethylammonium triheptanoyloxyborohydride , methyltriethylammonium triheptanoyloxyborohydride , propyltriethylammonium triheptanoyloxyborohydride , butyltriethylammonium triheptanoyloxyborohydride , pentyltriethylammonium triheptanoyloxyborohydride , hexyltriethylammonium triheptanoyloxyborohydride , benzyltriethylammonium triheptanoyloxyborohydride , methyltripropylammonium triheptanoyloxyborohydride , ethyltripropylammonium triheptanoyloxyborohydride , butyltripropylammonium triheptanoyloxyborohydride , pentyltripropylammonium triheptanoyloxyborohydride , hexyltripropylammonium triheptanoyloxyborohydride , benzyltripropylammonium triheptanoyloxyborohydride , methyltributylammonium triheptanoyloxyborohydride , ethyltributylammonium triheptanoyloxyborohydride , propyltributylammonium triheptanoyloxyborohydride , pentyltributylammonium triheptanoyloxyborohydride , hexyltributylammonium triheptanoyloxyborohydride , benzyltributylammonium triheptanoyloxyborohydride , S34816 methyltripentylammonium triheptanoyloxyborohydride , ethyltripentylammonium triheptanoyloxyborohydride , propyltripentylammonium triheptanoyloxyborohydride , butyltripentylammonium triheptanoyloxyborohydride , hexyltripentylammonium triheptanoyloxyborohydride , benzyltripentylammonium triheptanoyloxyborohydride , methyltrihexylammonium triheptanoyloxyborohydride , ethyltrihexylammonium triheptanoyloxyborohydride , propyltrihexylammonium triheptanoyloxyborohydride , butyltrihexylammonium triheptanoyloxyborohydride , pentyltrihexylammonium triheptanoyloxyborohydride and, benzyltrihexylammonium triheptanoyloxyborohydride . (0023) The reaction of a compound (1), a compound (2) and a compound (3) is carried out by mixing a compound (1), a compound (2) and a compound (3) .

The reaction of a compound (1), a compound (2) and a compound (3) is preferably conducted in the presence of a solvent .

The solvent includes ester solvents such as ethyl acetate and butyl acetate, aromatic solvents such as toluene and xylene, ether solvents such as tert-butyl methyl ether, nitrile solvents such as acetonitrile , and S34816 alcohol solvents such as 2-propanol, preferably ester solvents, more preferably ethyl acetate.

The use amount of the solvent is usually 1 to 10 parts by weight, preferably 2 to 5 parts by weight with respect to 1 part by weight of a compound (1) . (0024) The use amount of a compound (2) is usually 1 to 5 mol, preferably 1 to 2 mol with respect to 1 mol of a compound ( 1 ) .

The use amount of a compound (3) is usually 1 to 5 mol, preferably 1 to 2 mol with respect to 1 mol of a compound ( 1 ) . (0025) The reaction time of the reaction of a compound (1) , a compound (2) and a compound (3) is usually 10 to 48 hours, preferably 10 to 24 hours. The reaction temperature of the reaction is usually 0 to 50°C, preferably 10 to 40°C. (0026) After completion of the reaction, a solution containing a compound (4) is usually obtained. The resultant solution containing a compound (4) can be purified if necessary by concentration and recrystallization, to give the compound (4) . (0027) The compound (4) includes 2- [4- S34816 (methoxyimino ) cyclohexyl] -2- (3,3,3-trifluoropropylsulfonyl ) acetonitrile, 2- [4- (ethoxyimino) cyclohexyl] -2- (3,3,3-trifluoropropylsulfonyl ) acetonitrile, 2- [4- (propoxyimino ) cyclohexyl] -2- (3,3,3-trifluoropropylsulfonyl ) acetonitrile, 2- [4- (butoxyimino ) cyclohexyl] -2- (3,3,3-trifluoropropylsulfonyl ) acetonitrile, 2- [4- (tert-butoxyimino ) cyclohexyl] -2- (3,3,3-trifluoropropylsulfonyl ) acetonitrile, 2- [4- (pentoxyimino ) cyclohexyl] -2- (3,3,3-trifluoropropylsulfonyl ) acetonitrile, 2- [4- (hexoxyimino ) cyclohexyl] -2-(3,3,4,4,4-pentafluoropropylsulfonyl ) acetonitrile and the like. (0028) [Process for obtaining compound (3)] As the compound (3), commercially available compounds may be used, or the compound (3) can be obtained by reacting a compound (5) and compound (6) .

S34816 The monovalent anion except for a hydroxide ion and an alkoxide ion) (hereinafter, referred to as monovalent anion in some cases) includes halide ions such as a fluoride ion, a chloride ion, a bromide ion and an iodide ion; halogenoid ions such as a cyanide ion, a thiocyanate ion, a selenocyanate ion, a tellurocyanate ion, an azide dithio carbonate ion, a cyanate ion, a fulminate ion and an azide ion; alkanesulfonate ions optionally having a fluorine atom such as a methane sulfonate ion and a trifluoromethane sulfonate ion; acetate ions optionally having a halogen atom such as a trifluoroacetate ion and a trichloroacetate ion; a nitrate ion; a perchlorate ion; tetrahaloborate ions such as a tetrafluoroborate ion and a tetrachloroborate ion; hexahalophosphate ions such as a hexafluorophosphate ion; hexahaloantimonate ions such as a hexafluoroantimonate ion and a hexachloroantimonate ion; pentahalostannate ions such as a pentafluorostannate ion and a pentachlorostannate ion; tetraarylborates optionally having a substituent such as tetraphenylborate , tetrakis (pentafluorophenyl ) borate and tetrakis [3, 5-bis (trifluoromethyl) phenyl] borate; a carbonate ion, and the like.

The monovalent anion is preferably a halide ion. (0030) The compound (5) includes tetramethylammonium S34816 chloride, tetraethylammonium chloride, tetrapropylammonium chloride, tetrabutylammonium chloride, tetraisobutylammonium chloride, tetrapentylammonium chloride, tetrahexylammonium chloride, ethyltrimethylammonium chloride, propyltrimethylammonium chloride, butyltrimethylammonium chloride, pentyltrimethylammonium chloride, hexyltrimethylammonium chloride, benzyltrimethylammonium chloride, methyltriethylammonium chloride, propyltriethylammonium chloride, butyltriethylammonium chloride, pentyltriethylammonium chloride, hexyltriethylammonium chloride, benzyltriethylammonium chloride, methyltripropylammonium chloride, ethyltripropylammonium chloride, butyltripropylammonium chloride, pentyltripropylammonium chloride, hexyltripropylammonium chloride, benzyltripropylammonium chloride, methyltributylammonium chloride, ethyltributylammonium chloride, propyltributylammonium chloride, pentyltributylammonium chloride, hexyltributylammonium chloride, benzyltributylammonium chloride, methyltripentylammonium chloride, ethyltripentylammonium chloride, propyltripentylammonium chloride, butyltripentylammonium chloride, hexyltripentylammonium chloride, benzyltripentylammonium chloride, methyltrihexylammonium chloride, ethyltrihexylammonium chloride, propyltrihexylammonium chloride, butyltrihexylammonium chloride, pentyltrihexylammonium chloride and benzyltrihexylammonium chloride.

As the compound (5), commercially available compounds may be used. (0031) The alkali metal ion includes a lithium ion, a sodium ion, a potassium ion, a rubidium ion and the like, preferably a sodium ion. (0032) As the compound (6), commercially available compounds may be used, alternatively, compounds obtained by reacting a compound represented by formula (7) (hereinafter, referred to as compound (7) in some cases) and a compound represented by formula (8) (hereinafter, referred to as compound (8) in some cases) may be used.

The compound (6) includes sodium triacetoxyborohydride , sodium tripropionyloxyborohydride, sodium tributanoyloxyborohydride, sodium tripentanoyloxyborohydride , sodium trihexanoyloxyborohydride , sodium triheptanoyloxyborohydride ; lithium triacetoxyborohydride, lithium tripropionyloxyborohydride , lithium tributanoyloxyborohydride , lithium tripentanoyloxyborohydride , lithium trihexanoyloxyborohydride , lithium triheptanoyloxyborohydride ; potassium triacetoxyborohydride, potassium tripropionyloxyborohydride , potassium tributanoyloxyborohydride , potassium tripentanoyloxyborohydride , potassium trihexanoyloxyborohydride , potassium triheptanoyloxyborohydride ; rubidium triacetoxyborohydride, rubidium tripropionyloxyborohydride , rubidium tributanoyloxyborohydride , rubidium tripentanoyloxyborohydride , rubidium trihexanoyloxyborohydride , rubidium triheptanoyloxyborohydride, and the like.

The compound (6) is preferably sodium triacetoxyborohydride . (0033) The compound (7) includes sodium borohydride, lithium borohydride, potassium borohydride and the like, preferably sodium borohydride.

The compound (8) includes acetic acid, propionic acid, butyric acid, pentanoic acid, hexanoic acid, heptanoic acid and the like, preferably acetic acid.

The reaction of a compound (7) and a compound (8) is carried out by mixing a compound (7) and a compound (8) .

The reaction time is usually 1 to 48 hours, preferably 3 to 24 hours. The reaction temperature is usually 0 to 50°C, preferably 0 to 20°C.

The use amount of a compound (8) is usually 3 to 5 mol, preferably 3 to 4 mol with respect to 1 mol of a compound ( 7 ) . (0034) The reaction is preferably conducted in the presence of a solvent.

The solvent includes ester solvents such as ethyl acetate and butyl acetate; aromatic solvents such as toluene and xylene; ether solvents such as tert-butylmethyl ether; nitrile solvents such as acetonitrile ; and alcohol solvents such as 2-propanol. Ester solvents are preferable, and ethyl acetate is more preferable.

The use amount of the solvent is usually 1 to 10 parts by weight, preferably 1 to 3 parts by weight with respect to 1 part by weight of a compound (7) .

The resultant reaction mixture containing a compound (6) may be reacted with a compound (5), alternatively, a compound (6) may be isolated from the mixture and then reacted with a compound (5) . For example, a compound (6) can be isolated by concentrating the resultant reaction S34816 mixture . (0035) The reaction of a compound (5) and a compound (6) is carried out by mixing a compound (5) and a compound (6) . The reaction time is usually 1 to 48 hours, preferably 3 to 24 hours. The reaction temperature is usually 0 to 80°C, preferably 20 to 50°C.

The use amount of a compound (5) is usually 1 to 5 mol, preferably 1 to 2 mol with respect to 1 mol of a compound ( 6 ) . (0036) The reaction of a compound (5) and a compound (6) is preferably conducted in the presence of a solvent.

The solvent includes ester solvents such as ethyl acetate and butyl acetate, aromatic solvents such as toluene and xylene, ether solvents such as tert-butyl methyl ether, nitrile solvents such as acetonitrile , and alcohol solvents such as 2-propanol, preferably ester solvents, more preferably ethyl acetate.

The use amount of the solvent is usually 1 to 10 parts by weight, preferably 1 to 3 parts by weight with respect to 1 part by weight of a compound (5) . (0037) A compound (3) may be isolated from the resultant reaction mixture and mixed with a compound (1) and a S34816 compound (2), alternatively, the reaction mixture itself may be mixed with a compound (1) and a compound (2) .

For example, a compound (3) can be isolated by concentrating the reaction mixture. The isolated compound (3) can be purified by usual purification means such as washing and re-crystallization. (0038) The compound (3) can be obtained also by reacting a compound (5) , a compound (7) and a compound (8) . (0039) The reaction of a compound (5), a compound (7) and a compound (8) is carried out by mixing a compound (5), a compound (7) and a compound (8) .

The reaction is preferably conducted in a non-aqueous system. The non-aqueous system denotes no use of water as a solvent. (0040) The reaction of a compound (5), a compound (7) and a compound (8) is preferably conducted in the presence of a solvent .

The solvent includes ester solvents such as ethyl acetate and butyl acetate, aromatic solvents such as toluene and xylene, ether solvents such as tert-butyl S34816 methyl ether, nitrile solvents such as acetonitrile , and alcohol solvents such as 2-propanol. Ester solvents are preferable, and ethyl acetate is more preferable.

The use amount of the solvent is usually 1 to 10 parts by weight, preferably 1 to 3 parts by weight with respect to 1 part by weight of a compound (5) . (0041) The reaction time is usually 1 to 48 hours, preferably3 to 24 hours. The reaction temperature is usually 0 to 80°C, preferably 10 to 50°C. (0042) The use amount of a compound (5) is usually 1 to 5 mol, preferably 1 to 2 mol with respect to 1 mol of a compound ( 7 ) .

The use amount of a compound (8) is usually 2 to 5 mol, preferably 3 to 4 mol with respect to 1 mol of a compound ( 7 ) . (0043) A compound (3) may be isolated from the resultant reaction mixture and mixed with a compound (1) and a compound (2), alternatively, the reaction mixture itself may be mixed with a compound (1) and a compound (2) .

For example, a compound (3) can be isolated by concentrating the reaction mixture. The isolated compound (3) can be purified by usual purification means such as S34816 washing and re-crystallization. (0044) The compound (3) can be obtained by mixing a compound (5) and a compound (7), and mixing the resultant mixture with a compound (8) .

Mixing is preferably conducted in a non-aqueous system.

Mixing of a compound (5) and a compound (7) is preferably conducted in the presence of a solvent.

The solvent includes ester solvents such as ethyl acetate and butyl acetate; aromatic solvents such as toluene and xylene; ether solvents such as tert-butyl methyl ether; nitrile solvents such as acetonitrile ; and alcohol solvents such as 2-propanol, preferably ester solvents, more preferably ethyl acetate.

The use amount of the solvent is usually 1 to 10 parts by weight, preferably 1 to 3 parts by weight with respect to 1 part by weight of a compound (5) . (0045) The total mixing time for mixing a compound (5) and a compound (7), then, mixing with a compound (8) is usually 1 to 48 hours, preferably 3 to 24 hours. The mixing S34816 temperature is usually 0 to 80°C, preferably 10 to 50°C.

The use amount of a compound (5) is usually 1 to 5 mol, preferably 1 to 2 mol with respect to 1 mol of a compound ( 7 ) .

The use amount of a compound (8) is usually 2 to 5 mol, preferably 3 to 4 mol with respect to 1 mol of a compound ( 7 ) . (0046) A compound (3) may be isolated from the resultant reaction mixture and mixed with a compound (1) and a compound (2), alternatively, the reaction mixture itself may be mixed with a compound (1) and a compound (2) .

For example, a compound (3) can be isolated by concentrating the reaction mixture. The isolated compound (3) can be purified by usual purification means such as washing and re-crystallization. (0047) The compound (3) can be obtained by reacting a compound (7) and a compound (8) to give a compound (6) and reacting the resultant compound (6) and a compound (5) .

The reaction is preferably conducted in a non-aqueous system.

S34816 The reaction is preferably conducted in the presence of a solvent.

The solvent includes ester solvents such as ethyl acetate and butyl acetate; aromatic solvents such as toluene and xylene; ether solvents such as tert-butyl methyl ether; nitrile solvents such as acetonitrile ; and alcohol solvents such as 2-propanol, preferably ester solvents, more preferably ethyl acetate.

The use amount of the solvent is usually 1 to 10 parts by weight, preferably 1 to 3 parts by weight with respect to 1 part by weight of a compound (5) . (0048) The total reaction time is usually 1 to 48 hours, preferably 3 to 24 hours. The reaction temperature is usually 0 to 80°C, preferably 10 to 50°C.

The use amount of a compound (5) is usually 1 to 5 mol, preferably 1 to 2 mol with respect to 1 mol of a compound ( 7 ) .

The use amount of a compound (8) is usually 2 to 5 mol, preferably 3 to 4 mol with respect to 1 mol of a compound ( 7 ) .

The use amount of a compound (5) is usually 1 to 5 mol, preferably 1 to 2 mol with respect to 1 mol of a compound ( 6 ) . (0049) S34816 A compound (3) may be isolated from the resultant reaction mixture and mixed with a compound (1) and a compound (2), alternatively, the reaction mixture itself may be mixed with a compound (1) and a compound (2) .

For example, a compound (3) can be isolated by concentrating the reaction mixture. The isolated compound (3) can be purified by usual purification means such as washing and re-crystallization.

(EXAMPLES) (0050) The present invention will be illustrated further in detail by examples below. (0051) (Example 1) Tetramethylammonium triacetoxyborohydride (201.8 g) was suspended in 300 g of ethyl acetate to give a mixture. Into 200 g of ethyl acetate were dissolved 100 g of 3,3,3-trifluoropropylsulfonylacetonitrile (content: 97.7%) and 123.1 g of 1 , 4-cyclohexanedione monooxime ether (content: 78.0%) to give a solution. The resultant solution was dropped into the resultant mixture over a period of 6 hours at 30°C. The resultant mixture was stirred for 15.5 hours. The resultant reaction mixture was diluted with ethyl acetate. At 30°C, the resultant mixture was washed with a S34816 % hydrochloric acid aqueous solution, a 1% acetic acid aqueous solution, a 23% sodium hydroxide aqueous solution and water sequentially. The resultant mixture was concentrated to give 245.1 g of an ethyl acetate solution of 2- [4- (methoxyimino ) cyclohexyl] -2- (3,3,3-trifluoropropylsulfonyl ) acetonitrile (content: 61.2%, yield: 94.7%) . (0052) (Example 2) Tetramethylammonium chloride (14.5 g) and sodium borohydride (5.0 g) were suspended in 32.5 g of ethyl acetate, to give a mixture. At 10°C, 23.3 g of acetic acid was dropped into the resultant mixture. The resultant mixture was heated up to 40°C, and stirred for 16 hours. The resultant reaction mixture was cooled down to 28°C, and an ethyl acetate solution containing 45 g of 3,3,3-trifluoropropylsulfonylacetonitrile (content: 36.1%) and 26.6 g of 1 , 4-cyclohexanedione monooxime ether (content: 64.2%) was dropped over a period of 6 hours. The resultant mixture was stirred for 20 hours. The resultant reaction mixture was diluted with ethyl acetate, and washed with a 5% hydrochloric acid aqueous solution, a 15% sodium hydroxide aqueous solution and water sequentially. The resultant mixture was concentrated, to give 56.9 g of an ethyl acetate solution of 2- [4- (methoxyimino) cyclohexyl] -2- S34816 (3,3, 3-trifluoropropylsulfonyl ) acetonitrile (content: 44.2%, yield: 95.6%). To the resultant ethyl acetate solution was added 2-butanol and the mixture was concentrated, to give 51.1 g of a 2-butanol solution of 2- [4- (methoxyimino ) cyclohexyl] -2- (3,3,3-trifluoropropylsulfonyl ) acetonitrile (content: 46.5%).

To the resultant 2-butanol solution were added 48.8 g of heptane and 34.2 g of 2-butanol, and the mixture was heated up to 60°C, to give a solution. The resultant solution was cooled down to 5°C at a rate of 10°C/hr, to give a suspension. Into the resultant suspension, 48.8 g of heptane was dropped over a period of 2 hours. The resultant mixture was filtrated to give a crystal. The resultant crystal was washed with a 10% 2-butanol/heptane solution, then, dried under reduced pressure, to give 21.9 g of 2- [4- (methoxyimino) cyclohexyl] -2- (3, 3, 3-trifluoropropylsulfonyl ) acetonitrile (content: 99.7%). (0053) (Example 3) Sodium borohydride (7.0 g) was mixed with 46.2 g of ethyl acetate to give a mixture. At 10°C, 33.1 g of acetic acid was dropped into the resultant mixture. The resultant mixture was heated up to 40°C, and stirred for 12 hours. A reaction mixture containing sodium triacetoxyborohydride was obtained. At the same temperature, to the resultant S34816 reaction mixture was added 20.2 g of tetramethylammonium chloride, and the mixture was stirred for 18 hours. A reaction mixture containing tetramethylammonium triacetoxyborohydride was obtained. Into the resultant reaction mixture, an ethyl acetate solution containing 65.0 g of 3 , 3 , 3-trifluoropropylsulfonylacetonitrile (content: 35.5%) and 37.4 g of 1 , 4-cyclohexanedione monooxime ether (content: 65.0%) was dropped over a period of 6 hours. The resultant mixture was stirred for 22 hours. The resultant reaction mixture was diluted with ethyl acetate, and washed with a 5% hydrochloric acid aqueous solution, a 24% sodium hydroxide aqueous solution and water sequentially, to give 226.4 g of an ethyl acetate solution containing 2- [4- (methoxyimino ) cyclohexyl] -2- (3,3,3-trifluoropropylsulfonyl ) acetonitrile (content: 15.8%, yield: 95.2%) . (0054) (Example 4) Sodium borohydride (11.9 g) was mixed with 78.9 g of ethyl acetate to give a mixture. At 10°C, 56.6 g of acetic acid was dropped into the resultant mixture. A reaction mixture containing sodium triacetoxyborohydride was obtained. Tetramethylammonium chloride (34.5 g) was mixed with 47.6 g of ethyl acetate, the resultant mixture was heated up to 40°C, and at the same temperature, the S34816 reaction mixture containing sodium alkoxyborohydride prepared above was dropped. The mixture was further stirred for 3 hours, to give a reaction mixture containing tetramethylammonium triacetoxyborohydride. The resultant reaction mixture was cooled down to 27.5°C, and an ethyl acetate solution containing 83.3 g of 3,3,3-trifluoropropylsulfonylacetonitrile (content: 39.9%) and 53.7 g of 1 , 4-cyclohexanedione monooxime ether (content: 65.2%) was dropped over a period of 6 hours. The resultant mixture was stirred for 36 hours. The resultant reaction mixture was diluted with ethyl acetate, and washed with a 5% hydrochloric acid aqueous solution, a 24% sodium hydroxide aqueous solution and water sequentially, to give 343.2 g of an ethyl acetate solution containing 2- [4-(methoxyimino ) cyclohexyl] -2- (3,3,3-trifluoropropylsulfonyl ) acetonitrile (content: 12.8%, yield: 90.1%) . (0055) (Example 5) Sodium borohydride (5.5 g) and benzyltriethylammonium chloride (33.4 g) were mixed with 72.5 g of ethyl acetate to give a mixture. At 10°C, 26.3 g of acetic acid was dropped into the resultant mixture. The resultant mixture was heated up to 40°C, and stirred for 13 hours. A reaction mixture containing benzyltriethylammonium triacetoxyborohydride was obtained. Into the resultant reaction mixture, an ethyl acetate solution containing 49.4 g of 3 , 3 , 3-trifluoropropylsulfonylacetonitrile (content: 39.5%) and 32.6 g of 1 , 4-cyclohexanedione monooxime ether (content: 58.9%) was dropped over a period of 6 hours at 27.5°C. The resultant mixture was stirred for 15 hours. The resultant reaction mixture was diluted with ethyl acetate, and washed with a 5% hydrochloric acid aqueous solution, a 24% sodium hydroxide aqueous solution and water sequentially, to give 179.7 g of an ethyl acetate solution containing 2- [4- (methoxyimino ) cyclohexyl] -2- (3,3,3-trifluoropropylsulfonyl ) acetonitrile (content: 17.1%, yield: 96.9%) . (0056) (Example 6) Sodium borohydride (9.8 g) was mixed with 54.6 g of ethyl acetate to give a mixture. At 10°C, 46.5 g of acetic acid was dropped into the resultant mixture. A reaction mixture containing sodium triacetoxyborohydride was obtained. Benzyltriethylammonium chloride (59.9 g) was mixed with 53.2 g of ethyl acetate, and the resultant mixture was heated up to 40°C. Into the resultant mixture, the reaction mixture containing sodium triacetoxyborohydride was dropped at 40°C. The resultant mixture was stirred for 3 hours, to give a reaction mixture containing benzyltriethylammonium triacetoxyborohydride. The resultant reaction mixture was cooled down to 27.5°C. Into the resultant mixture, an ethyl acetate solution containing 70.0 g of 3,3,3-trifluoropropylsulfonylacetonitrile (content: 39.0%) and 44.1 g of 1 , 4-cyclohexanedione monooxime ether (content: 65.2%) was dropped over a period of 6 hours. The resultant mixture was stirred for 36 hours. The resultant reaction mixture was diluted with ethyl acetate, and washed with a 5% hydrochloric acid aqueous solution, a 24% sodium hydroxide aqueous solution and water sequentially, to give 245.2 g of an ethyl acetate solution of 2- [4-(methoxyimino ) cyclohexyl] -2- (3,3,3-trifluoropropylsulfonyl ) acetonitrile (content: 17.4%, yield: 96.4%) . (0057) (Example 7) Sodium borohydride (4.8 g) and 29.0 g of benzyltriethylammonium chloride were mixed with 68.1 g of ethyl acetate to give a mixture. At 10°C, 22.8 g of acetic acid was dropped into the resultant mixture. The resultant mixture was heated up to 40°C, and stirred for 18 hours. A reaction mixture containing benzyltriethylammonium triacetoxyborohydride was obtained. Into the resultant reaction mixture, an ethyl acetate solution containing 49.0 Document Name)

Claims (7)

1. A process for producing a nitrile compound represented by formula (4) : wherein R and R are as defined below, the process comprising: reacting together a compound represented by formula (1) : wherein R 1 represents an alkyl group having 1 to 6 carbon atoms and optionally having a halogen atom, a compound represented by formula (2) : wherein R represents an alkyl group having 1 to 6 carbon atoms, and a compound represented by formula (3) : S34816 wherein R3 , R4 and R5 each independently represents an alkyl group having 1 to 20 carbon atoms, R6 represents an alkyl group having 1 to 20 carbon atoms or a benzyl group optionally having a substituent, and R7 each independently represents an alkyl group having 1 to 20 carbon atoms.

2. The process according to Claim 1, wherein R6 is an alkyl group having 1 to 20 carbon atoms or a benzyl group.

3. The process according to Claim 1 or 2, the process further comprising: reacting a compound represented by formula (5) : wherein R3 , R4 , R5 and R6 are as defined above, and X~ represents a monovalent anion except for a hydroxide ion and an alkoxide ion, with a compound represented by formula (6) : wherein R is as defined above, and M represents an alkali metal ion, to give the compound represented by formula (3) . S34816

4. The process according to Claim 1 or 2, the process further comprising: reacting a compound represented by formula (5) : wherein R3 , R4 , R5 and R6 are as defined above, and X~ represents a monovalent anion except for hydroxide ion and an alkoxide ion, a compound represented by formula (7) : M ® B0H4 m(7) wherein M+ represents an alkali metal ion, and a compound represented by formula (8) : wherein R is as defined above, to give the compound represented by formula (3) .

5. The process according to Claim 4, wherein the compound represented by formula (5), the compound represented by formula (7) and the compound represented by formula (8) are reacted in a non-aqueous system.

6. The process according to Claim 1 or 2, the process further comprising: reacting a compound represented by formula (5) : S34816 wherein R3 , R4 , R5 and R6 are as defined above, and X~ represents a monovalent anion except for a hydroxide ion and an alkoxide ion, with a compound represented by formula (7) : M BH4 (' ) wherein M+ represents an alkali metal ion, mixing the resultant mixture with a compound by formula wherein R7 is as defined above, to give the compound represented by formula (3) .

7. The process according to Claim 1 or 2, the process further comprising: reacting a compound represented by formula (7) : M BH4 (7) wherein M+ represents an alkali metal ion, with a compound represented by formula (8) :