反応 #1351644

反応方程式

water

3-(trans-4-(trans-4-propylcyclohexyl)cyclohexyl)propionic acid

2,3-difluoro-4-ethoxyphenol

dicyclohexylcarbodiimide

→

2,3-difluoro-4-ethoxyphenyl 3-(trans-4-(trans-4-propylcyclohexyl)cyclohexyl)propionate

収率 102.5%

溶媒

dichloromethane

dichloromethane

反応条件

後処理

1. 1
   その他In a 3-L three-neck flask equipped with a stirrer
2. 2
   その他to prepare a solution, which
3. 3
   workup.ADDITIONwas added dropwise to the reaction mixture at room temperature
4. 4
   workup.ADDITIONAfter dropwise adding
5. 5
   workup.STIRRINGthe solution was stirred at room temperature for 14 hours
6. 6
   ろ過were filtered
7. 7
   洗浄the filtrate was washed with 300 ml of 3M hydrochloric acid, 300 ml of water, 300 ml of a saturated aqueous sodium hydrogencarbonate solution and 600 ml of water
8. 8
   乾燥dried over anhydrous magnesium sulfate
9. 9
   workup.DISTILLATIONThe solvent was distilled off from the reaction solution
10. 10
    その他to obtain 56.4 g of a concentrated substance, which
11. 11
    その他was then purified by means of a silica gel column chromatography with a mixed solvent of heptane/ethyl acetate (7/3)

実験手順

In a 3-L three-neck flask equipped with a stirrer, a thermometer and a dropping funnel, 32.0 g (114.9 mmol) of 3-(trans-4-(trans-4-propylcyclohexyl)cyclohexyl)propionic acid and 20.0 g (114.9 mmol) of 2,3-difluoro-4-ethoxyphenol were dissolved in 1000 ml of dichloromethane at room temperature under nitrogen atmosphere, and 15.4 g (126.4 mmol) of 4-dimethylaminopyridine was added thereto. The solution was stirred for 30 minutes thereafter, and then 26.1 g (126.4 mmol) of dicyclohexylcarbodiimide was dissolved in 400 ml of dichloromethane to prepare a solution, which was added dropwise to the reaction mixture at room temperature. After dropwise adding, the solution was stirred at room temperature for 14 hours. 500 ml of water was added to the reaction solution, insoluble materials were filtered, and then the filtrate was washed with 300 ml of 3M hydrochloric acid, 300 ml of water, 300 ml of a saturated aqueous sodium hydrogencarbonate solution and 600 ml of water and dried over anhydrous magnesium sulfate. The solvent was distilled off from the reaction solution under reduce pressure to obtain 56.4 g of a concentrated substance, which was then purified by means of a silica gel column chromatography with a mixed solvent of heptane/ethyl acetate (7/3) used as a developing solvent to obtain 51.4 g of 2,3-difluoro-4-ethoxyphenyl 3-(trans-4-(trans-4-propylcyclohexyl)cyclohexyl)propionate as colorless crystals.

出典