Acetic Acid → 6-(3-Hydroxymethyl-phenyl)-hexanoic Acid Methyl Ester

Participants

Reaction Steps

To a solution of 6-[3-(tert-butyl-diphenyl-silanyloxymethyl)-phenyl]-hexanoic acid methyl ester (2.37 g, 5 mmol) in THF (10 mL) is added acetic acid (283 μL, 5 mmol) and 1M TBAF (5 mL). The solution is stirred for 2 hrs then diluted with EtOAc/ether (1:1). The organic layer is washed with water, brine, dried over MgSO4 and concentrated. The residue is purified by flash chromatography (eluting with 35% ethyl acetate/hexanes) to give 1.12 g of title compound. MS (EI) 236 (M+).

Provenance & Evidence