Citric Acid → HCID 11553414, compound

Participants

Reaction Steps

A solution of 2-(5-benzyloxy-4′-trifluoromethyl-biphenyl-3-yl)-2-methyl-propionic acid methyl ester (0.12 g, 0.28 mmol) in THF (4 ml) was treated at room temperature with a solution of KOH (0.17 g, 3.00 mmol) in methanol and water (3 ml, 6:1). After two days the mixture was acidified with citric acid and extracted with EtOAc. The combined organic extracts were washed with NaHCO3 solution (sat aq), brine, dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography (EtOAc:petroleum ether) to give 2-(5-benzyloxy-4′-trifluoromethyl-biphenyl-3-yl)-2-methyl-propionic acid (0.045 g, 0.11 mmol) as a white solid in 39% yield. 1H NMR (d4-MeOD) 7.79-7.71 (m, 4H), 7.50-7.46 (m, 2H), 7.42-7.36 (m, 2H), 7.35-7.29 (m, 1H), 7.25-7.23 (m, 1H), 7.17-7.14 (m, 1H), 7.08-7.05 (m, 1H), 5.17 (s, 2H), 1.59 (s, 6H); LCMS method (A), RT=4.5 min.

Provenance & Evidence