Water → Methyl 4-(2-benzyloxybenzyl)benzoate

Participants

Reaction Conditions

Reaction Steps

In a nitrogen stream, triethylsilane (2.27 mL, 13.5 mmol) and a boron trifluoride-diethyl ether complex (1.52 mL, 11.88 mmol) were added to a solution of 4-[(2-benzyloxyphenyl)-hydroxymethyl]benzoic acid methyl ester (4.15 g, 11.9 mmol) in acetonitrile (22.7 mL) at −40° C. and the mixture solution was stirred at the same temperature for 1.5 hours and further at 0° C. for 30 minutes. Water was added thereto and the mixture was extracted with methylene chloride. The organic layer was washed with a saturated sodium chloride aqueous solution and dried (anhydrous magnesium sulfate), and then the solvent was distilled under reduced pressure. The obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:10)] to obtain the title compound (2.39 g, 62%).

Provenance & Evidence