3-Phenylbenzo[b]thiophene-2-carbaldehyde → 1-(3-Phenylbenzo[b]thiophen-2-yl)ethanol

Participants

Reaction Steps

To a solution of 3-phenylbenzo[b]thiophene-2-carbaldehyde (430 mg, 1.87 mmol) in THF (10 mL) cooled to −78° C. and under a nitrogen atmosphere was added 3.0M MeMgBr in diethyl ether (1.24 mL) and stirring was continued for 30 min. The reaction mixture was quenched with a saturated solution of NH4Cl (20 mL) and slowly warmed to RT. The mixture was extracted with EtOAc (×2) and the combined organic layers were washed with water, then dried (Na2SO4) and concentrated in vacuo affording 1-(3-phenylbenzo[b]thiophen-2-yl)ethanol as a white solid (472 mg, quantitative). 1H NMR (CDCl3, 400 MHz): δ 7.88-7.84 (1H, m), 7.52-7.28 (8H, m), 5.21 (1H, q, J=6.35 Hz), 2.03 (1H, s), 1.59 (3H, d, J=6.63 Hz).

Provenance & Evidence