Borane;tetrahydrofuran → N-[4-(hydroxymethyl)-3-methylphenyl]acetamide

Participants

Reaction Steps

4-(Acetylamino)-2-methylbenzoic acid (2 g, 10.4 mmol) was suspended in THF (50 mL) and borane-THF complex (1M in THF, 26 mL, 26 mmol) added drop-wise over 15 minutes. The reaction mixture was stirred under argon overnight. The reaction mixture was quenched with water (51 mL) and extracted with EtOAc (×3). The combined organics were dried and concentrated. The crude product was purified by chromatography. Elution with 0-100% EtOAc/petroleum ether yielded the title compound as a cream solid (0.379 g). δH (MeOD, 400 MHz) 7.36 (2H, d), 7.25 (1H, d), 4.57 (2H, s), 2.31 (3H, s), 2.10 (3H, s). MS (ES+): MH+ 180.2.

Provenance & Evidence