O-Methylhydroxylamine hydrochloride → 2-[2-{(1-ethoxyethyl)oxymethyl}phenyl]-2-methoxyimino-N-methylacetamide

Participants

Reaction Steps

Methoxyamine hydrochloride (0.50 g, 0.006 mol) was dissolved in methanol (6 ml), and a 28% sodium methoxide-methanol solution (1.45 g, 0.0075 mol) was added to the solution to obtain a suspension. A mixed solution of 2-[2-{(1-ethoxyethyl)oxymethyl}phenyl]-N-methyl-2-oxoacetamide (0.80 g, 0.003 mol) and methanol (3 ml) was added to the suspension, and the mixture was stirred under reflux for 1 hour. After completion of the reaction, half-saturated brine (150 ml) was added, and the mixture was extracted with dichloromethane (100 ml) twice. The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (ethyl acetate/n-hexane) to obtain an E/Z mixture of 2-[2-{(1-ethoxyethyl)oxymethyl}phenyl]-2-methoxyimino-N-methylacetamide (0.82 g, Yield: 92.8%) as a colorless oil.

Provenance & Evidence