Ammonium Chloride → 3-Methylbenzo(b)thiophene-2-methanol

Participants

Reaction Steps

To an ice-cold suspension of lithium aluminum hydride (103 mg, 2.72 mmol) in THF (4.4 mL) was added dropwise over 15 minutes under N2 atmosphere, a solution of the above-mentioned methyl 3-methylbenzothiophene-2-carboxylate (560 mg, 2.72 mmol) in THF (1 mL). The mixture was stirred under ice-cooling for 45 minutes, then at room temperature for 5 minutes, to which was added dropwise under ice-cooling saturated aqueous ammonium chloride solution. The mixture was filtered through a layer of Celite, washed with ethyl acetate. Combined organic layers were washed with saturated brine. After drying over anhydrous sodium sulfate, the solvent was removed under reduced pressure to give the titled compound as a white crystal (483 mg, yield 99%).

Provenance & Evidence