Hydrochloric Acid → ethyl(2RS,3RS)-3-[4-(benzyloxy)phenyl]-3-hydroxy-2-[3-(1,1,2,2-tetrafluoroethoxy) benzyl]propanoate

Participants

Reaction Steps

To a solution of zinc chloride (18.9 g, 139 mmol) in diethyl ether (500 ml) was added sodium borohydride (10.5 g, 278 mmol), and the mixture was stirred at room temperature for 30 min. Insoluble material was filtered off. To the filtrate was added a solution of ethyl 3-[4-(benzyloxy)phenyl]-3-oxo-2-[3-(1,1,2,2-tetrafluoroethoxy)benzyl]propanoate (35.0 g, 69.4 mmol) in diethyl ether (200 ml) at 0° C., and the mixture was stirred for 30 min. 1N Hydrochloric acid was added to the reaction solution to stop the reaction. Then, water (500 ml) was added and the mixture was extracted with ethyl acetate (500 ml×2). The extract was washed with water and saturated brine, dried (anhydrous magnesium sulfate) and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) and recrystallized from ethyl acetate-hexane to give the objective substance (30.3 g, 86%).

Provenance & Evidence