CN111285827A - Preparation method of novel difurane compound - Google Patents

Preparation method of novel difurane compound Download PDF

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CN111285827A
CN111285827A CN202010116285.0A CN202010116285A CN111285827A CN 111285827 A CN111285827 A CN 111285827A CN 202010116285 A CN202010116285 A CN 202010116285A CN 111285827 A CN111285827 A CN 111285827A
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郭凯
王海鑫
李振江
陈恺
罗子堃
刘博�
李勇强
屈圆圆
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Nanjing Tech University
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/36—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/40—Radicals substituted by oxygen atoms
    • C07D307/42—Singly bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
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Abstract

The invention belongs to the field of organic synthesis, and particularly relates to a preparation method of a novel difuran compound, wherein a furan ring compound shown in a formula 1 and a carbonyl-containing compound shown in a formula 2 are adopted to generate the difuran compound shown in a formula 4 under the catalysis of o-diphenyldisulfonimide shown in a formula 3.

Description

Preparation method of novel difurane compound
Technical Field
The invention belongs to the field of organic synthesis, and particularly relates to a preparation method of a novel difurane compound.
Background
The widespread use of fossil resources has led to a decrease in their supply and a rise in oil prices over the past century. And carbon dioxide from the combustion of fossil fuels may also contribute to global climate change. Due to these problems, great attention is currently paid to renewable and sustainable resources. In particular, furan compounds derived from carbohydrate biomass that can be photosynthetic from atmospheric carbon dioxide are of interest as promising alternatives to aromatic compounds that have so far relied entirely on petroleum reforming processes. For example, it is believed that 2, 5-furandicarboxylic acid (FDCA) may be substituted for terephthalic acid, which is a diacid monomer used in the preparation of polyethylene terephthalate. There are a large number of polymeric carbohydrates, such as cellulose and hemicellulose, worldwide that can be depolymerized to yield monosaccharides, hexoses (glucose from cellulose) and pentoses (xylose from hemicellulose). After catalytic dehydration reactions, monosaccharides can be converted to furfural intermediates [ 5-hydroxymethyl-2-furfural (HMF) from hexoses, and 2-furfural from pentoses ]. Subsequent oxidation or reduction reactions can produce various furan compounds.
Bisphenol a (BPA) and bisphenol a monomers are used industrially to synthesize materials such as Polycarbonate (PC) and epoxy resins. Have been used for the 60 s for the manufacture of plastic bottles, drinking cups for infants, inner coatings for food and beverage cans. However, bisphenol a produces materials that degrade during use to produce toxic materials that can have a wide range of undesirable effects on living organisms. With the development of industrialization, the wide application of plastic products and epoxy resins increases the demand for BPA, which leads to the increase of the discharge amount of BPA pollutants in the environment and causes serious environmental pollution. A bis-furan compound (polymerizable monomer) having a structure in which two furan rings are bonded together by a hydrocarbon group or the like has attracted attention as a bio-based raw material having a structure similar to that of a bisphenol-type compound. Because the furan ring has rigidity similar to that of a benzene ring and has similar properties, polymers such as polyester and the like prepared by replacing bisphenol A compounds with bisphenol A furan monomers can have certain rigidity and higher glass transition temperature, so that the application range of the polymer is wider, and the polymer has great market prospect.
Regarding the synthesis of difuranic acid, known methods including Gandini et al mostly start from furfural, and obtain bisphenol a type furan monomer through catalytic alkylation reaction, deprotection, and reduction.
Disclosure of Invention
In order to solve the problems, the invention aims to construct a novel method for synthesizing the difuran compound, which is a synthesis process that uses a safer catalyst and enables reaction conditions to be heated and/or post-treatment of the reaction to be simpler.
The specific scheme is as follows:
a preparation method of a novel difuran compound comprises the following steps that a furan ring compound shown as a formula 1 and a carbonyl-containing compound shown as a formula 2 are catalyzed by o-diphenyldisulfonimide shown as a formula 3 to generate the difuran compound shown as a formula 4:
Figure BDA0002391596280000021
wherein:
R1and R2The same or different substituents selected from hydrogen, alkyl groups of 1 to 3 carbon atoms, and substituted or unsubstituted phenyl groups, wherein the alkyl groups include saturated or unsaturated alkyl groups;
R3selected from alkyl groups having 1 to 3 carbon atoms,An ester group, an aldehyde group or an amino group substituted alkyl group having 1 to 3 carbon atoms. The alkyl group as used herein includes saturated or unsaturated alkyl groups, and the ester group refers to-COOR, where R is typically a non-hydrogen group such as an alkyl group.
Preferably, R1And R2Identical or different substituents selected from hydrogen, methyl, ethyl, or phenyl; r3Selected from methyl, carbomethoxy, i.e. -COOCH3Ethyl formate, i.e., -COOCH2Or aminomethyl2HN-CH2-。
Preferably, the furan ring compound shown in the formula 1 and the carbonyl-containing compound shown in the formula 2 are respectively adopted to generate the bis-furan compound shown in the formula 4 under the catalysis of the o-diphenyldisulfonimide shown in the formula 3:
Figure BDA0002391596280000022
Figure BDA0002391596280000031
preferably, the reaction temperature of the preparation method is 80-110 ℃.
Preferably, the reaction of the preparation process is carried out in a polar aprotic solvent.
Preferably, the aprotic solvent should preferably be an aprotic solvent resistant to high temperatures of 80 ℃.
Preferably, the solvent of the preparation method is one or more of toluene, DMSO, DMF or xylene.
Preferably, the carbonyl-containing compound represented by formula 2 is slowly added to the furan ring compound represented by formula 1 during the reaction. The term "slow" is used herein in accordance with the size of the reaction scale. Where applicable at small laboratory scale, the addition may be at a rate of around one drop per second, but in scale-up applications, depending on scale, this is well known to those skilled in the art.
Has the advantages that:
compared with the prior art, the invention has at least one of the following advantages:
1. the reaction route is shorter, and the synthesis method is simpler;
2. the reaction condition is milder, and the operation is safer;
3. the reaction is greener, and the harmfulness is less;
4. the treatment after the reaction is simpler;
5. the substrate adaptability is wider;
6. the furan ring has aromaticity, can be derived from carbohydrates, has certain similarity with a benzene ring in property, and can be used for partially substituting monomers such as petroleum-based terephthalic acid, bisphenol A and the like.
Drawings
FIG. 1 is a nuclear magnetic hydrogen spectrum characterization diagram of the structure of the product M1 obtained in example 1
FIG. 2 is a nuclear magnetic carbon spectrum characterization chart of the structure of M1 product obtained in example 1
FIG. 3 is a nuclear magnetic hydrogen spectrum characterization chart of the structure of the product M7 obtained in example 9
DETAILED DESCRIPTION OF EMBODIMENT (S) OF INVENTION
In order to facilitate understanding for those skilled in the art, the concept of the present invention will be further described with reference to the following examples. The following specific description of the embodiments is not to be construed as limiting the invention, but merely as a prelude to the more detailed description that is presented for the understanding of the principles of the invention. Tables 1 and 2 below show the purchase information for the materials and equipment used in the examples below, all of which were purchased from the market.
TABLE 1 reagent sources and purities
Figure BDA0002391596280000041
TABLE 2 instruments and apparatus
Figure BDA0002391596280000051
In the formula 1, wherein R3When alkyl, 1 may be 1a methylfuran; wherein R is3When it is an ester group, 1 may be 1b furoic acid methyl ester, 1c furoic acid ethyl ester(ii) a Wherein R is3When aminoalkyl, 1 may be 1d furfuryl amine.
In the formula 2, wherein R1＝R2When H, structure 2a is formaldehyde; wherein R is1＝H,R2＝CH3When structure 2b is acetaldehyde; wherein R is1＝H,R2＝CH2-CH3When the structure is 2c, the compound is propionaldehyde; wherein R is1＝H,R2When Ph, the structure is 2d, is benzaldehyde; wherein R1 ═ CH3,R2＝CH3When the structure is 2e, it is acetone.
Example 1
5.00g (0.04mol) of methyl 2-furoate (1b) was sufficiently dissolved in 20ml of a toluene solution, and 0.88g (0.004mol) of phthalimide (c) was added to the toluene solution. The mixture was stirred at room temperature to dissolve it sufficiently. 1.5 equivalents (0.06mol) of acetaldehyde (2b) were weighed into a constant pressure dropping funnel and dropped into the above toluene solution one drop per second. After the dropwise addition, the temperature is raised to 90 ℃, and the reaction is stirred for 5 hours. During this time, the reaction was monitored by TLC (PE: EA: 5: 1). When the starting point disappeared, the solution was spin dried. The product was subjected to column chromatography on silica gel column. The pure product M1 (white solid) obtained was dried by vacuum oven and weighed to yield ≈ 85%. (the nuclear magnetic structure is characterized in the attached figures 1 and 2).
Example 2
5.00g (0.04mol) of methyl 2-furoate (1b) was sufficiently dissolved in 20ml of a toluene solution, and 0.88g (0.004mol) of phthalimide (c) was added to the toluene solution. The mixture was stirred at room temperature to dissolve it sufficiently. 1.5 equivalents (0.06mol) of acetaldehyde (2b) were weighed into a constant pressure dropping funnel and dropped into the above toluene solution one drop per second. After the dropwise addition, the temperature is raised to 80 ℃, and the reaction is stirred for 5 hours. During this time, the reaction was monitored by TLC (PE: EA: 5: 1). When the starting point disappeared, the solution was spin dried. The product was subjected to column chromatography on silica gel column. The pure product M1 (white solid) obtained was dried by vacuum oven and weighed to yield ≈ 72%.
Example 3
5.00g (0.04mol) of methyl 2-furoate (1b) was sufficiently dissolved in 20ml of a toluene solution, and 0.88g (0.004mol) of phthalimide (c) was added to the toluene solution. The mixture was stirred at room temperature to dissolve it sufficiently. 1.5 equivalents (0.06mol) of acetaldehyde (2b) were weighed into a constant pressure dropping funnel and dropped into the above toluene solution one drop per second. After the dropwise addition, the temperature is raised to 100 ℃, and the reaction is stirred for 5 hours. During this time, the reaction was monitored by TLC (PE: EA: 5: 1). When the starting point disappeared, the solution was spin dried. The product was subjected to column chromatography on silica gel column. The pure product M1 (white solid) obtained was dried by vacuum oven and weighed to yield ≈ 86%.
Example 4
5.00g (0.04mol) of methyl 2-furoate (1b) was sufficiently dissolved in 20ml of a toluene solution, and 0.88g (0.004mol) of phthalimide (c) was added to the toluene solution. The mixture was stirred at room temperature to dissolve it sufficiently. 1.5 equivalents (0.06mol) of acetaldehyde (2b) were weighed into a constant pressure dropping funnel and dropped into the above toluene solution one drop per second. After the dropwise addition, the temperature is raised to 110 ℃, and the reaction is stirred for 5 hours. During this time, the reaction was monitored by TLC (PE: EA: 5: 1). When the starting point disappeared, the solution was spin dried. The product was subjected to column chromatography on silica gel column. The pure product M1 (white solid) obtained was dried by vacuum oven and weighed to yield ≈ 84%.
Example 5
5.61g (0.04mol) of ethyl 2-furoate (1c) was dissolved in 20ml of a toluene solution, and 0.88g (0.004mol) of phthalimide (c) was added to the toluene solution. The mixture was stirred at room temperature to dissolve it sufficiently. 1.5 equivalents (0.06mol) of acetone (2e) were weighed into a constant pressure dropping funnel and dropped into the above toluene solution one drop per second. After the dropwise addition, the temperature is raised to 90 ℃, and the reaction is stirred for 5 hours. During this time, the reaction was monitored by TLC (PE: EA: 5: 1). When the starting point disappeared, the solution was spin dried. The product was subjected to column chromatography on silica gel column. The pure product M9 (white solid) obtained was dried by vacuum oven and weighed to give a yield of approx.68%.
Example 6
5.00g (0.04mol) of methyl 2-furoate (1b) was sufficiently dissolved in 20ml of a toluene solution, and 0.88g (0.004mol) of phthalimide (c) was added to the toluene solution. The mixture was stirred at room temperature to dissolve it sufficiently. 1.5 equivalents (0.06mol) of propionaldehyde (2c) were weighed into an isopiestic dropping funnel and added dropwise one drop per second to the above toluene solution. After the dropwise addition, the temperature is raised to 90 ℃, and the reaction is stirred for 5 hours. During this time, the reaction was monitored by TLC (PE: EA: 5: 1). When the starting point disappeared, the solution was spin dried. The product was subjected to column chromatography on silica gel column. The pure product M3 (yellow solid) obtained was dried by vacuum oven and weighed to yield ≈ 70%.
Example 7
5.00g (0.04mol) of methyl 2-furoate (1b) was sufficiently dissolved in 20ml of a toluene solution, and 0.88g (0.004mol) of phthalimide (c) was added to the toluene solution. The mixture was stirred at room temperature to dissolve it sufficiently. 1.5 equivalents (0.06mol) of benzaldehyde (2d) were weighed into a constant pressure dropping funnel and dropped one drop per second into the above toluene solution. After the dropwise addition, the temperature is raised to 90 ℃, and the reaction is stirred for 5 hours. During this time, the reaction was monitored by TLC (PE: EA: 5: 1). When the starting point disappeared, the solution was spin dried. The product was subjected to column chromatography on silica gel column. The pure product M4 (yellow solid) obtained was dried by vacuum oven and weighed to give a yield of about 50%.
Example 8
3.28g (0.04mol) of 2-methylfuran (1a) was dissolved in 20ml of a toluene solution, and 0.88g (0.004mol) of phthalimide (c) was added to the toluene solution. The mixture was stirred at room temperature to dissolve it sufficiently. 1.5 equivalents (0.06mol) of acetaldehyde (2b) were weighed into a constant pressure dropping funnel and dropped into the above toluene solution one drop per second. After the dropwise addition, the temperature is raised to 90 ℃, and the reaction is stirred for 5 hours. During this time, the reaction was monitored by TLC (PE: EA: 5: 1). When the starting point disappeared, the solution was spin dried. The product was subjected to column chromatography on silica gel column. The pure product M5 (yellow liquid) obtained was dried in a vacuum oven and weighed to give a yield of about 80%.
Example 9
3.88g (0.04mol) of 2-furfurylamine (1d) was dissolved in 20ml of a toluene solution sufficiently, and 0.88g (0.004mol) of phthalimide (c) was added to the toluene solution. The mixture was stirred at room temperature to dissolve it sufficiently. 1.5 equivalents (0.06mol) of acetone (2e) were weighed into a constant pressure dropping funnel and dropped into the above toluene solution one drop per second. After the dropwise addition, the temperature is raised to 90 ℃, and the reaction is stirred for 5 hours. During this time, the reaction was monitored by TLC (PE: EA: 5: 1). When the starting point disappeared, the solution was spin dried. The crude product was dissolved in ethyl acetate, neutralized with 10% sodium hydroxide solution, and adjusted to PH 7-8. It was extracted three times with ethyl acetate, dried over anhydrous magnesium sulfate, filtered and distilled under reduced pressure to distill off the product to give pure product M7 (brown liquid), which was weighed to give a yield of about 50%. (the nuclear magnetic structure is characterized as shown in FIG. 3).
Example 10
3.28g (0.04mol) of 2-methylfuran (1a) was dissolved in 20ml of a toluene solution, and 0.88g (0.004mol) of phthalimide (c) was added to the toluene solution. The mixture was stirred at room temperature to dissolve it sufficiently. 1.5 equivalents (0.06mol) of acetone (2e) were weighed into a constant pressure dropping funnel and dropped into the above toluene solution one drop per second. After the dropwise addition, the temperature is raised to 90 ℃, and the reaction is stirred for 5 hours. During this time, the reaction was monitored by TLC (PE: EA: 5: 1). When the starting point disappeared, the solution was spin dried. The product was subjected to column chromatography on silica gel column. The pure product M6 (orange liquid) obtained was dried in a vacuum oven and weighed with a yield of about 80%.
Example 11
3.28g (0.04mol) of 2-methylfuran (1a) was dissolved in 20ml of a toluene solution, and 0.88g (0.004mol) of phthalimide (c) was added to the toluene solution. The mixture was stirred at room temperature to dissolve it sufficiently. 1.5 equivalents (0.06mol) of formaldehyde (2a) were weighed into a constant pressure dropping funnel and dropped into the above toluene solution one drop per second. After the dropwise addition, the temperature is raised to 90 ℃, and the reaction is stirred for 5 hours. During this time, the reaction was monitored by TLC (PE: EA: 5: 1). When the starting point disappeared, the solution was spin dried. The product was subjected to column chromatography on silica gel column. The pure product M11 (pale yellow liquid) obtained was dried by means of a vacuum oven and weighed to give a yield of approx.72%.
Example 12
5.00g (0.04mol) of methyl 2-furoate (1b) was sufficiently dissolved in 20ml of a toluene solution, and 0.88g (0.004mol) of phthalimide (c) was added to the toluene solution. The mixture was stirred at room temperature to dissolve it sufficiently. 1.5 equivalents (0.06mol) of acetaldehyde (2b) were weighed into a constant pressure dropping funnel and dropped into the above toluene solution one drop per second. After the dropwise addition, the temperature is raised to 90 ℃, and the reaction is stirred for 5 hours. During this time, the reaction was monitored by TLC (PE: EA: 5: 1). When the starting point disappeared, the solution was spin dried. The product was subjected to column chromatography on silica gel column. The resulting pure product M1 (white solid) was dried by vacuum oven.
M1 was dissolved in ethyl acetate solution and catalytically hydrolyzed with sodium hydroxide at 60 ℃ and the reaction was monitored by dot plate. After the reaction, the pH was adjusted to be acidic. Extraction with ethyl acetate was carried out three times, and drying over anhydrous magnesium sulfate, filtration and drying treatment by a vacuum oven gave pure product M8 (off-white solid), which was weighed to give a yield of approximately 60%.
The structure of M8 is:
Figure BDA0002391596280000081
example 13
5.00g (0.04mol) of methyl 2-furoate (1b) was sufficiently dissolved in 20ml of a toluene solution, and 0.88g (0.004mol) of phthalimide (c) was added to the toluene solution. The mixture was stirred at room temperature to dissolve it sufficiently. 1.5 equivalents (0.06mol) of acetaldehyde (2b) were weighed into a constant pressure dropping funnel and dropped into the above toluene solution one drop per second. After the dropwise addition, the temperature is raised to 90 ℃, and the reaction is stirred for 5 hours. During this time, the reaction was monitored by TLC (PE: EA: 5: 1). When the starting point disappeared, the solution was spin dried. The product was subjected to column chromatography on silica gel column. The obtained pure product M1 was dried in a vacuum oven.
M1 was dissolved in ethyl acetate solution and catalytically hydrolyzed with sodium hydroxide at 60 ℃ and the reaction was monitored by dot plate. After the reaction, the pH was adjusted to be acidic. The extract was extracted three times with ethyl acetate, dried over anhydrous magnesium sulfate, filtered, and then dried by a vacuum oven to obtain pure product M8.
The bis-furandioic acid M8 was reduced by catalytic hydrogenation of LiAlH4 to give the product M10 (pale yellow liquid).
The structure of M10 is:
Figure BDA0002391596280000082

Claims (7)

1. a preparation method of a novel difuran compound is characterized in that a furan ring compound shown as a formula 1 and a carbonyl-containing compound shown as a formula 2 generate the difuran compound shown as a formula 4 under the catalysis of o-diphenyldisulfonimide shown as a formula 3:
Figure FDA0002391596270000011
wherein:
R1and R2The same or different substituents are selected from hydrogen, alkyl with 1-3 carbon atoms and substituted or unsubstituted phenyl;
R3selected from alkyl with 1 to 3 carbon atoms, ester group, aldehyde group or alkyl with 1 to 3 carbon atoms substituted by amino.
2. The production method according to claim 1,
R1and R2Identical or different substituents from the group consisting of hydrogen, methyl, ethyl or phenyl;
R3selected from methyl, carbomethoxy or aminomethyl.
3. The preparation method according to claim 1, wherein the furan ring compound represented by formula 1 and the carbonyl group-containing compound represented by formula 2 are catalyzed by orthophthalimide represented by formula 3 to form a bis-furan compound represented by the following formula 4:
Figure FDA0002391596270000012
Figure FDA0002391596270000021
4. the preparation method according to claim 1, wherein the reaction temperature of the preparation method is 80-110 ℃.
5. The process according to claim 1, wherein the reaction is carried out in a polar aprotic solvent.
6. The method of claim 1, wherein the reaction is carried out in one or more solvents selected from toluene, DMSO, DMF, and xylene.
7. The method according to claim 1, wherein the carbonyl group-containing compound represented by formula 2 is slowly added to the furan ring-type compound represented by formula 1 during the reaction.
CN202010116285.0A 2019-12-08 2020-02-25 Preparation method of novel difurane compound Pending CN111285827A (en)

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Application publication date: 20200616