Ammonium Chloride → Ethyl 2-[5-benzyloxy-4'-(trifluoromethyl)biphenyl-3-yl]pentanoate

Participants

Reaction Steps

A solution of LDA (4.5 mL of 1.8 M in THF, 8 mmol) was added dropwise to a stirred solution of (5-Benzyloxy-4′-trifluoromethyl-biphenyl-3-yl)-acetic acid ethyl ester (3 g, 7.3 mmol) in THF (50 mL) at −78° C. The reaction mixture was stirred for 30 minutes at −78° C. before iodopropane (0.85 mL, 8.7 mmol) was added dropwise. The reaction mixture was allowed to warm to room temperature overnight. A saturated aqueous solution of ammonium chloride (10 mL) was carefully added and the residue was partitioned between EtOAc and water. The aqueous layers were extracted with EtOAc (×3). The combined organic layers were washed with water, 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)-pentanoic acid ethyl ester (2.2 g) as an oil in 66% yield.

Provenance & Evidence