Hydrochloric Acid → ethyl (2RS,3RS)-3-(4-fluorophenyl)-3-hydroxy-2-(3-trifluoromethylbenzyl)propionate

Beteiligte Stoffe

Reaktionsschritte

To a solution of anhydrous zinc chloride (7.4 g, 54.3 mmol) in diethyl ether (50 ml) was added sodium borohydride (4.11 g, 0.11 mol) and the mixture was stirred at room temperature for 2 hrs. The insoluble material was removed by filtration. To the filtrate was added a solution of ethyl 3-(4-fluorophenyl)-3-oxo-2-(3-trifluoromethylbenzyl)propionate (10 g, 27.1 mmol) in diethyl ether (20 ml) and the mixture was stirred at room temperature for 1 hr. 1N Hydrochloric acid was added to the reaction solution to terminate the reaction. The reaction solution was extracted with ethyl acetate (100 ml). The extract was washed with water and saturated aqueous sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1-5:1) to give ethyl (2RS,3RS)-3-(4-fluorophenyl)-3-hydroxy-2-(3-trifluoromethylbenzyl)propionate (7.9 g, 79%) as a colorless oil.

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