Sodium Hydroxide → (2RS,3RS)-3-(4-fluorophenyl)-3-hydroxy-2-((4-(trifluoromethyl)phenyl)methyl)propionic acid

Participants

Reaction Steps

To a solution of ethyl (2RS,3RS)-3-(4-fluorophenyl)-3-hydroxy-2-((4-(trifluoromethyl)phenyl)methyl)propionate (11.0 g, 29.7 mmol) in methanol (90 ml) was added 1N aqueous sodium hydroxide solution (59.6 ml, 59.6 mmol), and the mixture was stirred at room temperature for 6 hrs. The reaction solution was evaporated under reduced pressure, diluted with 1N hydrochloric acid (100 ml), and extracted with ethyl acetate (200 ml×2). The extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. Recrystallization from ethyl acetate-hexane gave (2RS,3RS)-3-(4-fluorophenyl)-3-hydroxy-2-((4-(trifluoromethyl)phenyl)methyl)propionic acid (8.6 g, 85%).

Provenance & Evidence