Chloromethyl ethyl ether → alpha-chloro-N-(ethoxymethyl)-N-(2,6-dimethoxyphenyl)acetamide

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To a mixture containing potassium hydride (2.2 g; 0.055 mole) in 50 ml. of tetrahydrofuran was added a solution of alpha-chloro-N-(2,6-dimethoxyphenyl)acetamide (11.5 g; 0.05 mole) in 250 ml. of tetrahydrofuran. Hydrogen gas evolved from the reaction mixture. To the reaction mixture was added an excess of (chloromethyl)ethyl ether (10 ml.) which caused the temperature of the reaction mixture to increase to 45° C. An excess of a sodium bicarbonate solution (100 ml.) was then added to the reaction mixture followed by the addition of 100 ml. of diethyl ether. The layers were separated and the organic ether layer was dried over magnesium sulfate, filtered and concentrated in vacuo to yield an amber oil. The amber oil was separated on a silica gel column using a 3:2 hexane:diethyl ether mixture as the eluant. Fractions containing a crude product were combined and concentrated in vacuo to yield a solid residue. The solid residue was taken up in pentane and the pentane solution was scratched until a white solid formed. The pentane solution containing the white solid was filtered and the white solid was recrystallized from heptane to yield alpha-chloro-N-(ethoxymethyl)-N-(2,6-dimethoxyphenyl)acetamide (3.0 g; 20.9% yield) having a melting point of 95°-97° C. and the following analysis:

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