1,2-Dichloroethane → N-Methoxy-2-(4-methoxyphenyl)-N-methylacetamide

Participants

Reaction Steps

To a solution of 4-methoxyphenylacetic acid (3.3 g, 20 mmole) in dry DMF (75 mL) was added N-methoxy-N-methylamine hydrochloride (1.95 g, 20 mmole), Et3N (3.1 mL, 22 mmole), HOBt H2O (1.95 g, 22 mmole), and EDC (2.7 g, 22 mmole). The solution was stirred at RT overnight, then was concentrated in vacuum. The residue was taken up in 5% Na2CO3 solution (10 mL) and extracted with CH2Cl2 (3×20 mL). The combined organic layers were dried over MgSO4, filtered and concentrated. The residue was chromatographed on silica gel (3% MeOH/CH2Cl2) to give the title compound (1.54 g, 37%) as white solid: MS (ES) m/e 210 (M+H)+.

Provenance & Evidence