反应详情

To a solution of zinc chloride (7.39 g, 54.2 mmol) in diethyl ether (150 ml) was added sodium borohydride (4.11 g, 108.5 mmol), and the mixture was stirred at room temperature for 30 min. The insoluble material was filtered off, and a solution of ethyl 3-oxo-3-(4-phenoxyphenyl)-2-((4-(trifluoromethyl)phenyl)methyl)propionate (10 g, 25.9 mmol) in diethyl ether (50 ml) was added to the filtrate. The mixture was stirred at room temperature for 30 min. 1N Hydrochloric acid was added to the reaction solution under ice-cooling to quench the reaction. Water (200 ml) was added, and the mixture was extracted with ethyl acetate (300 ml×2). The extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate) to give ethyl(2RS,3RS)-3-hydroxy-3-(4-phenoxyphenyl)-2-((4-(trifluoromethyl)phenyl)methyl)propionate (12.0 g, 100%) as a colorless oil.

1. filtrationThe insoluble material was filtered off
2. stirringThe mixture was stirred at room temperature for 30 min
3. temperaturecooling
4. customto quench
5. customthe reaction
6. extractionthe mixture was extracted with ethyl acetate (300 ml×2)
7. washThe extract was washed with water and saturated brine
8. dry with materialdried over anhydrous magnesium sulfate
9. customevaporated under reduced pressure
10. customThe residue was purified by silica gel column chromatography (ethyl acetate)