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

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Reaction Steps

To a suspension of zinc chloride anhydride (1.72 g, 12.6 mmol) in diethyl ether (20 ml) was added sodium borohydride (0.95 g, 25.2 mmol) by small portions, and the mixture was stirred for 1 hr. Insoluble material was removed by filtration, and washed with diethyl ether. The filtrate was ice-cooled, and a solution of ethyl 3-[4-(methylsulfonyl)phenyl]-3-oxo-2-[3-(1,1,2,2-tetrafluoroethoxy)benzyl]propanoate (3.0 g, 6.30 mmol) in diethyl ether (10 ml) was added. The mixture was stirred at room temperature for 1 hr. After ice-cooling again, 1N hydrochloric acid was added to terminate the reaction. The obtained mixture was extracted with ethyl acetate (100 ml), washed with water, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica gel chromatography (hexane:ethyl acetate=2:1-1:1) to give the objective substance (2.60 g, 86%) as a colorless oil.

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