Hydrochloric Acid → (2RS,3RS)-3-(4-fluorophenyl)-3-hydroxy-2-(4-methoxybenzyl)propionic acid

Participants

Reaction Steps

To a solution of ethyl (2RS,3RS)-3-(4-fluorophenyl)-3-hydroxy-2-(4-methoxybenzyl)propionate (22.8 g, 68.6 mmol) in methanol (100 ml) was added 2N aqueous sodium hydride solution (69 ml, 0.137 mol) and the mixture was stirred at room temperature for 4 hrs. The reaction solution was acidified with 6N hydrochloric acid, water (300 ml) was added, and the mixture was extracted with ethyl acetate (200 ml×2). The extract was washed with water, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was crystallized from a mixture of hexane and diethyl ether to give (2RS,3RS)-3-(4-fluorophenyl)-3-hydroxy-2-(4-methoxybenzyl)propionic acid (14.8 g, 71%).

Provenance & Evidence