Benzoic Acid → (2R)-1-(Biphenyl-4-yloxy)-4-(3-pyridyl)-2-butanol

Participants

Reaction Steps

Diethyl azodicarboxylate (0.123 ml) was added to a stirring solution of (2S)-4-(3-pyridyl)-1-[(4-phenyl)phenoxy]-butan-2-ol (0.25 g), triphenylphosphine (0.262 g) and benzoic acid (0.122 g) in tetrahydrofuran (10 ml) at 0° C. and the resulting solution was stirred for 1 hour. The mixture was concentrated under reduced pressure and the residue was redissolved in methanol (20 ml) and water (5 ml). Solid potassium hydroxide (0.112 g) was added and the reaction stirred for 2 hours before being poured into a solution of saturated aqueous sodium hydrogencarbonate. The mixture was extracted with ethyl acetate and the combined organic extracts were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give the title compound (0.22 g) as a solid that was recrystallised from ethyl acetate:hexane.

Provenance & Evidence