反应详情

To a solution of zinc chloride (3.35 g, 24.6 mmol) in diethyl ether (70 ml) was added sodium borohydride (1.86 g, 49.1 mmol) and the mixture was stirred at room temperature for 30 min. The insoluble material was filtered off. To the filtrate was added a solution of ethyl 3-(4-fluorophenyl)-3-oxo-2-((5-(trifluoromethyl)-2-furanyl)methyl)propionate (4.40 g, 12.3 mmol) in diethyl ether (30 ml) and the mixture was stirred at room temperature for 2 hrs. 1N Hydrochloric acid was added to the reaction solution under ice-cooling for quenching, water (100 ml) was further added, and the mixture as extracted with ethyl acetate (100 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 (hexane:ethyl acetate=4:1) to give ethyl (2RS,3RS)-3-(4-fluorophenyl)-3-hydroxy-2-((5-(trifluoromethyl)-2-furanyl)methyl)propionate (3.46 g, 78%).

1. filtrationThe insoluble material was filtered off
2. stirringthe mixture was stirred at room temperature for 2 hrs
3. temperaturecooling
4. customfor quenching
5. additionwater (100 ml) was further added
6. extractionthe mixture as extracted with ethyl acetate (100 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 (hexane:ethyl acetate=4:1)