Triethylamine → HCID 67865961, compound

Participants

Reaction Steps

To a stirred, cooled (0° C.) solution of 2.13 mL (0.017 mol) of ethyl malonyl chloride in 10 mL of methylene chloride under nitrogen was added dropwise a solution of 2.03 mL (0.017 mol) of m-anisidine in 10 mL of methylene chloride over a half-hour period. After the addition the reaction mixture was allowed to warm to room temperature and stir for 2 h. The reaction mixture was cooled to 0° C. and a solution of 2.36 mL (0.017 mol) of triethylamine in 10 mL of methylene chloride was added dropwise over 2 h. Additional methylene chloride was added to keep the slurry of salts stirring efficiently. After the addition the reaction mixture was kept cold by placing it in the freezer. After 12 h the reaction was allowed to warm to room temperature and was immediately washed with water three times to remove the salts. The organic layer was dried over magnesium sulfate and filtered. Removal of solvent gave a crude oil. Purification by flash-chromatography (silica gel, 25% ethyl acetate/hexane eluent) afforded 2.5 g (64% yield) of ethyl N-3-methoxyphenylmalonamide as a red oil.

Provenance & Evidence