Ethanol → 3-(Hydroxymethyl)-N,N-dimethylbenzamide

Participants

Reaction Steps

Under ice cooling, sodium borohydride (264 mg, 6.97 mmol) was added to an ethanol (15 ml) solution of methyl 3-(N,N-dimethylcarbamoyl)benzoate (289 mg, 1.39 mmol). The temperature of the resulting mixture was allowed to rise back to room temperature and then, stirring was conducted at 50° C. for 14 hours. After the reaction mixture was cooled back to room temperature, it was ice cooled. Sodium borohydride (264 mg, 6.97 mmol) was added and the mixture was stirred at 50° C. for 6 hours. The reaction mixture was ice cooled, and then added with water, followed by concentration under reduced pressure. The residue thus obtained was added with water, followed by extraction with methylene chloride. The extract was dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was subjected to chromatography on a silica gel column, and the fraction obtained from the methanol:methylene chloride (=1:30) eluate was concentrated under reduced pressure, whereby the title compound (196 mg, 79%) was obtained as a colorless oil.

Provenance & Evidence