Dichloromethane → 2-cyclopropyl-N-methoxy-N-methylacetamide

Participants

Reaction Steps

A 500 mL round bottom flask was charged with cyclopropylacetic acid (9.87 g, 98.6 mmol) (available from Oakwood) and DCM (200 mL). To the stirred solution was added 1,1′-carbonyldiimidazole (19.2 g, 118 mmol) portionwise (vigorous gas evolution). The yellow solution was stirred for 30 minutes at room temperature, and to it was added N,O-dimethylhydroxylamine hydrochloride (11.5 g, 118 mmol) (available from Aldrich) in one portion. The heterogeneous, white mixture was stirred overnight and diluted with ether (300 mL). The organics were washed with 1 N HCl (2×150 mL), saturated aqueous NaHCO3 (2×150 mL) and brine (1×150 mL), dried (MgSO4), and concentrated to afford 84.B (11.9 g, 84.3% yield) as a colorless liquid. The crude product was used without further purification.

Provenance & Evidence