Sodium hydride → 4-(2-Thienylmethoxymethyl)-2-(2-methylphenyl)benzoic acid methyl ester

Participants

Reaction Steps

To a suspension in DMF (3.5 mL) of sodium hydride (60% in mineral oil, 52 mg, 1.3 mmol) was added 2-thiophenemethanol (0.135 mL, 1.4 mmol) and the reaction mixture was stirred for 1.25 hours. 4-bromomethyl-2-(2-methylphenyl)benzoic acid methyl ester (0.35 mL, 1.2 mmol) was added and the reaction mixture was stirred for 2 hours. The reaction mixture was partitioned between water and ether. The aqueous phase was extracted with ether. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. Chromatography on silica gel (3% ethyl acetate-hexane) gave 4-(2-thienylmethoxymethyl)-2-(2-methylphenyl)benzoic acid methyl ester (250 mg).

Provenance & Evidence