1-Hydroxybenzotriazole → 2-(3,4-Dimethoxyphenoxy)-N-methoxy-N-methylacetamide

Participants

Reaction Steps

To a mixture of CHCl3 (100 mL) with 2-(3,4-dimethoxyphenoxy)acetic acid (4.244 g), N,O-dimethylhydroxyamine hydrochloride (2.341 g), WSC.HCl (4.984 g) and HOBt.H2O (3.513 g), Et3N (3.62 mL) was added and the mixture was stirred at room temperature for 20 hours. The reaction mixture was concentrated, H2O (400 mL) was added, and the organic layer extracted with AcOEt (500 mL) was washed successively with saturated aqueous sodium dicarbonate (400 mL), water (400 mL) and brine (400 mL), dried (MgSO4), filtered and concentrated to give a crude product, which was further purified by silica gel chromatography (AcOEt) to give the titled compound (4.01 g, pale brown oil.)

Provenance & Evidence