CN113072536B - Method for preparing 2-phenyl-3-benzoyl benzodihydrogen selenium substituted pyridine compound without metal catalysis - Google Patents
Method for preparing 2-phenyl-3-benzoyl benzodihydrogen selenium substituted pyridine compound without metal catalysis Download PDFInfo
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Abstract
The invention discloses a method for preparing 2-phenyl-3-benzoyl benzodihydrogen selenium pyridine compounds shown in formula (III) without metal catalysis, which is characterized in that the preparation methodThe method comprises the following steps: 2-seleno-hydroxybenzaldehyde compounds shown in a formula (I) and phenyl styryl ketone compounds shown in a formula (II) react fully in DMSO by taking sodium ethoxide as a catalyst to obtain 2-phenyl-3-benzoyl benzodihydro-selenopyridine compounds. The method has the advantages of no use of metal catalyst, simple operation, convenient post-treatment, meeting the requirement of green synthesis and the like, and has important application prospect in the industrial field of synthesis of pharmaceutical intermediates related to organic selenium compounds.
Description
Technical Field
The invention belongs to the technical field of chemical intermediate preparation, and particularly relates to a method for preparing 2-phenyl-3-benzoyl benzodihydrogen selenopyridine compounds without metal catalysis.
Background
The organic selenium compound has important physiological functions and has important effects on human health and disease treatment. Especially after more than half a century of research, the human beings have discovered and recognized the wide and important functions of the organic selenium compounds. Scientists at home and abroad use organic selenium compounds as the king of vital fire, heart protection, liver protection and anticancer. Especially, scientists have found a series of important findings in the research of the relationship between organic selenium compounds and cardiovascular diseases, immune functions and the like, so that the development and utilization of organic selenium resources to produce selenium-rich farm animal products and the provision of natural selenium-rich health-care foods for selenium-deficient areas become new hotspots for the development of health-care food industry and the medical field in China gradually.
The reported preparation method of the organic selenium compound is mainly obtained through multi-step coupling and oxidation, has the defects of more reaction steps, low reaction efficiency, easy generation of a series of byproducts which are difficult to treat in the reaction process and the like, causes irreparable pollution and damage to the environment, and does not meet the requirements of modern green synthesis. The method does not need a metal catalyst, and avoids the toxic action of the metal catalyst. The method for efficiently preparing the 2-phenyl-3-benzoyl benzodihydro-selenopyridine compound by adopting the sodium alkoxide with low price and high catalytic efficiency as the catalyst. Has the advantages of no metal catalyst, low cost, simple operation, convenient post-treatment, meeting the requirement of green synthesis and the like, and has important application prospect in the industrial field of the synthesis of pharmaceutical intermediates related to organic selenium compounds.
Disclosure of Invention
Aiming at the problems in the prior art, the invention aims to provide a method for preparing 2-phenyl-3-benzoyl benzodihydrogen selenopyridine compounds without metal catalysis.
The invention is realized by the following technical scheme:
a method for preparing 2-phenyl-3-benzoyl benzodihydro-selenopyridine compounds shown in formula (III) without metal catalysis is characterized in that the preparation method comprises the following steps: the 2-seleno-hydroxybenzaldehyde compound shown in the formula (I) and the phenyl styryl ketone compound shown in the formula (II) react fully in an organic solvent by taking sodium alcoholate as a catalyst to obtain a product, and the product is treated to obtain a 2-phenyl-3-benzoyl benzodihydro-selenopyridine compound; the sodium alcoholate salt is sodium ethylate, and the organic solvent is dimethyl sulfoxide (DMSO);
in the reaction formula, the substituent R is selected from one of the following groups: hydrogen, chlorine, bromine, etc.; substituent R1Selected from one of the following: hydrogen, methyl, methoxy; substituent R2Selected from one of the following: hydrogen, methoxy, trifluoromethyl.
Preferably, the proportion of the 2-seleno-hydroxybenzaldehyde compounds and the phenyl styryl ketone compounds is 10 mmol: 10 mmol.
Preferably, the proportion of the 2-selenobenzaldehyde compound, the phenyl styryl ketone compound and the sodium ethoxide is 10 mmol: 10 mmol: 20 mmol.
Preferably, the ratio of the 2-seleno-hydroxybenzaldehyde compounds, the phenyl styryl ketone compounds and the solvent DMSO is 10 mmol: 10 mmol: 30 mL.
Preferably, the equivalent ratio of the 2-seleno-hydroxybenzaldehyde compounds to the phenyl styryl ketone compounds is 1: 1.
preferably, the reaction temperature is 100 ℃ and the reaction time is 8 hours.
Preferably, the specific method of post-treatment consists of the following steps:
1) and (3) extraction: after the reaction product is cooled to room temperature at normal temperature, 20mL of saturated sodium chloride aqueous solution is added into the reaction product, then ethyl acetate is used for extraction for 3 times, 20mL of the ethyl acetate is used for each time, and the extraction liquid is combined;
2) concentration: drying the extract with anhydrous sodium sulfate, and rotary drying with rotary evaporator to obtain concentrate;
3) adsorbing the obtained concentrate by using column chromatography silica gel, adding the concentrate into a 200-mesh 300-mesh chromatography silica gel column, and adding normal hexane: performing flash column chromatography on ethyl acetate according to a certain proportion, combining eluent, performing rotary drying on a rotary evaporator, and pumping by an oil pump to obtain the product 2-phenyl-3-benzoyl benzodihydroselenopyridine compound.
Preferably, the drying time in step 2) is 8 hours.
Preferably, the volume ratio of the n-hexane to the ethyl acetate in the step 3) is 2:1-1: 1.
Drawings
FIG. 1 is a drawing of product 3a of the invention1H NMR spectrum;
FIG. 2 shows the product 3a of the present invention13C NMR spectrum;
FIG. 3 is a drawing showing a reaction product 3b of the present invention1H NMR spectrum;
FIG. 4 shows the product 3b of the present invention13C-NMR spectrum;
FIG. 5 shows the product 3c of the present invention1H NMR spectrum;
FIG. 6 shows the product 3c of the present invention13C-NMR spectrum;
FIG. 7 shows the product 3d of the present invention1H NMR spectrum;
FIG. 8 shows the product 3d of the present invention13C NMR spectrum;
FIG. 9 shows the product 3e of the present invention1H NMR spectrum;
FIG. 10 shows the product 3e of the present invention13C-NMR spectrum;
FIG. 11 shows the present inventionOf product 3f1H NMR spectrum;
FIG. 12 shows the product 3f of the present invention13C NMR spectrum;
FIG. 13 shows 3g of the product of the present invention1H NMR spectrum;
FIG. 14 shows 3g of the product of the present invention13C-NMR spectrum;
FIG. 15 shows the product of the present invention for 3h1H NMR spectrum;
FIG. 16 shows the product of the present invention for 3h13C NMR spectrum.
Detailed Description
The present invention will be described in more detail with reference to specific examples.
According to the synthetic method, 10mmol of 2-selenium hydroxyl benzaldehyde compound 1 and 10mmol of phenyl styryl ketone compound 2 are sequentially added into a 50mL round-bottom flask, then 30mL of DMSO and 20mmol of sodium ethoxide are sequentially added, and the mixture is stirred for 8 hours at 100 ℃. After cooling, 20mL of saturated sodium chloride aqueous solution is added into the system, extraction is carried out for 3 times by ethyl acetate, 20mL of saturated sodium chloride aqueous solution is carried out each time, organic phases are combined, after drying by anhydrous sodium sulfate, solvent is evaporated, and the pure product of the 2-phenyl-3-benzoyl benzo dihydroselenopyridine 3 is obtained by 200-mesh silica gel column chromatography, wherein the yield is 80-89%. Specific examples and characterization data are as follows.
Example 1: preparation of product 3a
In a 50mL round-bottomed flask, 2 mmol of seleno-hydroxybenzaldehyde and 10mmol of phenylstyryl ketone were added successively at room temperature, 30mL of DMSO and 20mmol of sodium ethoxide were added successively, and the mixture was stirred at 100 ℃ for 8 hours. After cooling, 20mL of saturated sodium chloride aqueous solution is added into the system, extraction is carried out for 3 times by ethyl acetate, 20mL of saturated sodium chloride aqueous solution is carried out each time, organic phases are combined, after drying by anhydrous sodium sulfate, solvent is evaporated, and the pure product of the 2-phenyl-3-benzoyl benzo dihydroselenopyridine compound 3a is obtained by silica gel column chromatography with 200-mesh and 300-mesh.
3a1The H NMR spectrum is shown in figure 1,13the C NMR spectrum is shown in FIG. 2.
Phenyl(2-phenyl-2H-selenochromen-3-yl)methanone(3a)Pale yellow solid；mp 156-158℃；
1H NMR(CDCl3,400MHz)δ7.70-7.68(m,2H),7.58-7.56(dd,J＝7.6Hz,2.4Hz,1H),7.44(d,J＝7.6Hz,2H),7.39(s,1H),7.29-7.18(m,8H),7.14-7.11(m,1H),5.48(s,1H)；13C NMR(CDCl3,100MHz)δ195.8,142.0,140.1,138.2,133.3,132.8,132.0,131.2,130.9,130.5,129.3,128.8,128.5,127.9,126.7,125.8,40.3；
HRMS(m/z)calculated for C22H16NaOSe[M+Na]+:399.0264,found:399.0266.
Example 2: preparation of product 3b
In a 50mL round-bottomed flask were added 2 mmol of seleno-hydroxybenzaldehyde and 10mmol of phenyl-4-methyl styryl ketone in turn at room temperature, followed by 30mL of DMSO and 20mmol of sodium ethoxide in that order and stirring was carried out at 100 ℃ for 8 hours. After cooling, 20mL of saturated sodium chloride aqueous solution is added into the system, extraction is carried out for 3 times by ethyl acetate, 20mL of saturated sodium chloride aqueous solution is carried out each time, organic phases are combined, after drying by anhydrous sodium sulfate, solvent is evaporated, and the pure product of the 2-phenyl-3-benzoyl benzo dihydroselenopyridine compound 3b is obtained by silica gel column chromatography with 200-mesh and 300-mesh.
3b1The H NMR spectrum is shown in FIG. 3,13the C NMR spectrum is shown in FIG. 4.
Phenyl(2-(p-tolyl)-2H-selenochromen-3-yl)methanone(3b)Pale yellow solid；mp 117-119℃；
1H NMR(CDCl3,400MHz)δ7.62-7.60(m,2H),7.49-7.45(dd,J＝6.0Hz,1.6Hz,1H),7.40-7.37(d,J＝6.4Hz,2H),7.30(s,1H),7.18-7.14(m,3H),7.09-7.07(d,J＝6.4Hz,2H),7.06-7.05(dd,J＝6.2Hz,1.2Hz,1H),6.94-6.92(d,J＝6.4Hz,2H),5.36(s,1H),2.17(s,3H)；13C NMR(CDCl3,100MHz)δ195.9,140.0,139.1,138.2,137.5,133.5,132.8,132.0,131.1,130.9,130.5,129.5,129.3,128.5,127.8,126.6,125.7,40.1,21.2；
HRMS(m/z)calculated for C23H18NaOSe[M+Na]+:413.0421,found:413.0423.
Example 3: preparation of product 3c
In a 50mL round-bottomed flask were added 2 mmol of seleno-hydroxybenzaldehyde and 10mmol of phenyl-3-methoxystyryl ketone in this order at room temperature, followed by 30mL of DMSO and 20mmol of sodium ethoxide in this order, and the mixture was stirred at 100 ℃ for 8 hours. After cooling, 20mL of saturated sodium chloride aqueous solution is added into the system, extraction is carried out for 3 times by ethyl acetate, 20mL of saturated sodium chloride aqueous solution is carried out each time, organic phases are combined, after drying by anhydrous sodium sulfate, solvent is removed by evaporation, and the pure product of the 2-phenyl-3-benzoyl benzo dihydroselenopyridine compound 3c is obtained by silica gel column chromatography with 200-mesh and 300-mesh.
3c1The H NMR spectrum is shown in FIG. 5,13the C NMR spectrum is shown in FIG. 6.
(2-(3-Methoxyphenyl)-2H-selenochromen-3-yl)(phenyl)methanone(3c)Yellow solid；mp 147-149℃；
1H NMR(CDCl3,400MHz)δ7.70-7.69(m,2H),7.57-7.55(d,J＝7.6Hz,1H),7.46-7.44(d,J＝7.6Hz,2H),7.38(s,1H),7.27-7.20(m,3H),7.14-7.10(m,2H),6.88-6.86(d,J＝8.0Hz,1H),6.82(s,1H),6.73-6.72(dd,J＝8.4Hz,2.4Hz,1H),5.45(s,1H),3.68(s,3H)；13C NMR(CDCl3,100MHz)δ195.8,159.8,143.5,140.2,138.2,133.3,132.8,132.0,131.2,130.9,130.5,129.8,129.3,128.5,127.7,125.8,119.1,113.1,112.6,55.2,40.2；
HRMS(m/z)calculated for C23H18NaO2Se[M+Na]+:429.0370,found:429.0372.
Example 4: preparation of product 3d
In a 50mL round-bottomed flask, 2 mmol of seleno-hydroxybenzaldehyde and 10mmol of phenyl-3, 4, 5-trimethoxy styryl ketone were added in succession at room temperature, 30mL of DMSO and 20mmol of sodium ethoxide were then added in succession, and stirring was carried out at 100 ℃ for 8 hours. After cooling, 20mL of saturated sodium chloride aqueous solution is added into the system, extraction is carried out for 3 times by ethyl acetate, 20mL of saturated sodium chloride aqueous solution is carried out each time, organic phases are combined, after drying by anhydrous sodium sulfate, solvent is removed by evaporation, and the pure product of the 2-phenyl-3-benzoyl benzo dihydroselenopyridine compound 3d is obtained by silica gel column chromatography with 200-mesh and 300-mesh.
3d1The H NMR spectrum is shown in FIG. 7,13the C NMR spectrum is shown in FIG. 8.
Phenyl(2-(3,4,5-trimethoxyphenyl)-2H-selenochromen-3-yl)methanon e(3d)Brownish viscous liquid；
1H NMR(CDCl3,400MHz)δ7.72-7.70(m,2H),7.58-7.57(dd,J＝7.6Hz,1.6Hz,1H),7.50-7.46(d,J＝8.0Hz,2H),7.39(s,1H),7.32-7.21(d,J＝7.2Hz,1H),7.28-7.26(m,2H),7.16-7.12(m,1H),6.51(s,2H),5.40(s,1H),3.76(s,3H),3.67(s,6H)；13C NMR(CDCl3,100MHz)δ195.9,153.2,139.9,138.1,137.6,137.5,133.8,132.9,132.1,131.2,130.6,129.3,128.6,127.9,125.9,103.7,60.9,56.0,40.6；
HRMS(m/z)calculated for C25H22O4NaSe[M+Na]+:489.0581,found:489.0583.
Example 5: preparation of product 3e
In a 50mL round-bottomed flask were charged 2 mmol of seleno-hydroxybenzaldehyde and 10mmol of phenyl-4-chlorostyryl ketone in this order at room temperature, followed by 30mL of DMSO and 20mmol of sodium ethoxide in this order and stirring at 100 ℃ for 8 hours. After cooling, 20mL of saturated sodium chloride aqueous solution is added into the system, extraction is carried out for 3 times by ethyl acetate, 20mL of saturated sodium chloride aqueous solution is carried out each time, organic phases are combined, after drying by anhydrous sodium sulfate, solvent is evaporated, and the pure product of the 2-phenyl-3-benzoyl benzodihydro-selenopyridine compound 3e is obtained by 200-mesh and 300-mesh silica gel column chromatography.
3e1The H NMR spectrum is shown in FIG. 9,13the C NMR spectrum is shown in FIG. 10.
(2-(4-Chlorophenyl)-2H-selenochromen-3-yl)(phenyl)methanone(3e)Yellow viscous liquid；
1H NMR(CDCl3,400MHz)δ7.70-7.68(m,2H),7.58-7.57(dd,J＝7.6Hz,2.0Hz,1H),7.47-7.45(d,J＝7.6Hz,2H),7.41(s,1H),7.26-7.24(m,3H),7.23-7.22(m,5H),5.41(s,1H)；13C NMR(CDCl3,100MHz)δ195.7,140.5,140.4,138.0,133.6,133.0,132.4,132.1,131.4,131.0,130.4,129.3,128.9,128.6,128.1,127.8,126.0,39.8；
HRMS(m/z)calculated for C22H15OClNaSe[M+Na]+:432.9874,found:432.9876.
Example 6: preparation of product 3f
In a 50mL round-bottomed flask, 2 mmol of seleno-hydroxybenzaldehyde and 10mmol of phenyl-2-bromostyryl ketone were added in succession at room temperature, 30mL of DMSO and 20mmol of sodium ethoxide were then added in succession, and stirring was carried out at 100 ℃ for 8 hours. After cooling, 20mL of saturated sodium chloride aqueous solution is added into the system, extraction is carried out for 3 times by ethyl acetate, 20mL of saturated sodium chloride aqueous solution is carried out each time, organic phases are combined, after drying by anhydrous sodium sulfate, solvent is evaporated, and the pure product of the 2-phenyl-3-benzoyl benzodihydro-selenopyridine compound 3f is obtained by silica gel column chromatography with 200-mesh and 300-mesh.
3f1The H NMR spectrum is shown in FIG. 11,13the C NMR spectrum is shown in FIG. 12.
(2-(2-Bromophenyl)-2H-selenochromen-3-yl)(phenyl)methanone(3f)Pale yellow solid；mp 148-150℃；
1H NMR(CDCl3,400MHz)δ7.73-7.71(m,2H),7.61-7.55(m,3H),7.48-7.45(d,J＝7.2Hz,2H),7.30-7.28(d,J＝7.2Hz,1H),7.23-7.12(m,3H),7.06-7.01(m,3H),5.86(s,1H)；13C NMR(CDCl3,100MHz)δ195.2,141.8,139.6,137.9,133.8,132.5,132.2,132.1,131.4,131.0,130.5,129.3,129.1,128.6,128.2,127.7,127.6,126.0,122.9,40.0；
HRMS(m/z)calculated for C22H15OBrNaSe[M+Na]+:476.9369,found:476.9371.
Example 7: preparation of product 3g
In a 50mL round-bottomed flask were charged 2 mmol of seleno-hydroxybenzaldehyde and 10mmol of 4-methylphenylstyryl ketone in turn at room temperature, followed by 30mL of DMSO and 20mmol of sodium ethoxide in that order and stirred at 100 ℃ for 8 hours. After cooling, 20mL of saturated sodium chloride aqueous solution is added into the system, extraction is carried out for 3 times by ethyl acetate, 20mL of saturated sodium chloride aqueous solution is carried out each time, organic phases are combined, after drying by anhydrous sodium sulfate, solvent is evaporated, and 3g of pure 2-phenyl-3-benzoyl benzodihydrophthalocyclopyridine compound is obtained by silica gel column chromatography with 200-mesh and 300-mesh.
3g1The H NMR spectrum is shown in FIG. 13,13the C NMR spectrum is shown in FIG. 14.
(2-Phenyl-2H-selenochromen-3-yl)(p-tolyl)methanone(3g)Yellow viscous liquid；
1H NMR(CDCl3,400MHz)δ7.63-7.61(m,2H),7.38(s,1H),7.28-7.27(m,7H),7.22-7.17(m,3H),7.12-7.11(dd,J＝6.0Hz,1.2Hz,1H),5.46(s,1H),2.43(s,3H)；
13C NMR(CDCl3,100MHz)δ,195.6,142.8,142.1,139.5,135.4,133.5,132.7,131.0,130.8,130.6,129.6,129.2,128.8,127.74,127.72,126.7,125.8,40.5,21.7；
HRMS(m/z)calculated for C23H18ONaSe[M+Na]+:413.0421,found:413.0423.
Example 6: preparation of product 3h
In a 50mL round-bottomed flask, 2 mmol of seleno-hydroxybenzaldehyde and 10mmol of 3-bromophenyl styryl ketone were added successively at room temperature, 30mL of DMSO and 20mmol of sodium ethoxide were added successively, and the mixture was stirred at 100 ℃ for 8 hours. After cooling, 20mL of saturated sodium chloride aqueous solution is added into the system, extraction is carried out for 3 times by ethyl acetate, 20mL of saturated sodium chloride aqueous solution is carried out each time, organic phases are combined, after drying by anhydrous sodium sulfate, solvent is removed by evaporation, and the 2-phenyl-3-benzoyl benzodihydro-selenopyridine compound is obtained by 200-mesh and 300-mesh silica gel column chromatography for 3 hours.
3h1The H NMR spectrum is shown in FIG. 15,13the C NMR spectrum is shown in FIG. 16.
(3-Bromophenyl)(2-phenyl-2H-selenochromen-3-yl)methanone(3h)Brownish viscous liquid；
1H NMR(CDCl3,400 MHz)δ7.80-7.79(m,1H),7.68-7.67(d,J＝6.4Hz,1H),7.59-7.57(d,J＝6.0 Hz,1H),7.38(s,1H),7.33-7.31(d,J＝6.0Hz,1H),7.27-7.24(m,5H),7.22-7.18(m,3H),7.15-7.12(m,1H),5.43(s,1H)；13C NMR(CDCl3,100 MHz)δ194.2,141.8,140.8,140.1,134.8,133.0,132.9,132.0,131.5,131.1,130.3,130.0,128.8,127.9,127.8,127.7,126.7,125.9,122.8,40.2；
HRMS(m/z)calculated for C22H16OBrSe[M+H]+:454.9550,found:454.9552.
Claims (9)
1. A method for preparing 2-phenyl-3-benzoyl benzodihydro-selenopyridine compounds shown in formula (III) without metal catalysis is characterized in that the preparation method comprises the following steps: the 2-seleno-hydroxybenzaldehyde compound shown in the formula (I) and the phenyl styryl ketone compound shown in the formula (II) react fully in an organic solvent by taking sodium alcoholate as a catalyst to obtain a product, and the product is treated to obtain a 2-phenyl-3-benzoyl benzodihydro-selenopyridine compound; the sodium alcoholate salt is sodium ethylate, and the organic solvent is dimethyl sulfoxide;
in the reaction formula, the substituent R is selected from one of the following groups: hydrogen, chlorine, bromine; substituent R1Selected from one of the following: hydrogen, methyl, methoxy; substituent R2Selected from one of the following: hydrogen, methoxy, trifluoromethyl.
2. The method for preparing 2-phenyl-3-benzoyl benzodihydro selenopyridines compound according to claim 1, wherein the ratio of the 2-selenobenzaldehyde compound to the phenyl styryl ketone compound is 10 mmol: 10 mmol.
3. The method for preparing 2-phenyl-3-benzoyl benzodihydro selenopyridines compound according to claim 1, wherein the ratio of the 2-selenobenzaldehyde compound, the phenyl styryl ketone compound and the sodium ethoxide is 10 mmol: 10 mmol: 20 mmol.
4. The method for preparing 2-phenyl-3-benzoyl benzodihydro selenopyridines compound according to claim 1, wherein the ratio of the 2-selenobenzaldehyde compound, the phenyl styryl ketone compound and the solvent DMSO is 10 mmol: 10 mmol: 30 mL.
5. The method for preparing 2-phenyl-3-benzoyl benzodihydro selenopyridines compound according to claim 1, wherein the equivalent ratio of the 2-selenoxybenzaldehyde compound to the phenylstyrene compound is 1: 1.
6. the method for preparing 2-phenyl-3-benzoyl chromafenopridine compounds according to claim 1, wherein the reaction temperature is 100 ℃ and the reaction time is 8 hours.
7. The method for preparing 2-phenyl-3-benzoyl benzodihydro selenopyridines compound according to claim 1, characterized in that the specific method of post-treatment comprises the following steps:
1) and (3) extraction: after the reaction product is cooled to room temperature at normal temperature, 20mL of saturated sodium chloride aqueous solution is added into the reaction product, then ethyl acetate is used for extraction for 3 times, 20mL of the ethyl acetate is used for each time, and the extraction liquid is combined;
2) concentration: drying the extract with anhydrous sodium sulfate, and rotary drying with rotary evaporator to obtain concentrate;
3) adsorbing the obtained concentrate by using column chromatography silica gel, adding the concentrate into a 200-mesh 300-mesh chromatography silica gel column, and adding normal hexane: performing flash column chromatography on ethyl acetate according to a certain proportion, combining eluent, performing rotary drying on a rotary evaporator, and pumping by an oil pump to obtain the product 2-phenyl-3-benzoyl benzodihydroselenopyridine compound.
8. The method for preparing 2-phenyl-3-benzoyl chroman-pyridine compounds with no metal catalysis in claim 7, wherein the drying time in step 2) is 8 hours.
9. The method for preparing 2-phenyl-3-benzoyl benzodihydro-selenopyridines compound under metal-free catalysis in claim 7, wherein the volume ratio of n-hexane to ethyl acetate in the step 3) is 2:1-1: 1.
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