Methyl propionate → 3-(4-Benzyloxy-phenyl)-3-hydroxy-2-methyl-propionic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

LDA (1.3 mL, 2.6 mmol) was added to a solution of methyl propionate (0.22 g, 2.6 mmol) in THF (5 mL) cooled to −78° C. under nitrogen atmosphere. The reaction was stirred for 30 min, and then 4-benzyloxy-benzaldehyde (0.50 g, 2.4 mmol) in THF (5 mL) was added. The reaction was stirred at −78° C. for 5 min, and then allowed to warm to room temperature and stirred overnight. The reaction was partitioned between ethyl acetate and 1N HCl. The organic layer was washed with brine, dried over magnesium sulfate, and concentrated to give an oil. The product was purified by FCC on silica gel eluting ethyl acetate:hexane (15:85 to 25:75) gradient to give 3-(4-benzyloxy-phenyl)-3-hydroxy-2-methyl-propionic acid methyl ester (0.12 g, 16%) as an oil. MS found: (M+H)+=301.

Provenance & Evidence