Chloroacetyl chloride → 2-[2-(N-benzyl-N-chloroacetylamino)-1-hydroxyethyl]-2-methyl-1,3-dioxolane

Participants

Reaction Steps

To a solution of 2-(2-benzylamino-1-hydroxyethyl)-2-methyl-1,3-dioxolane (5.55 g) in a mixture of tetrahydrofuran (50 ml) and water (50 ml) was added a solution of chloroacetyl chloride (1.9 ml) in tetrahydrofuran (4 ml) under ice-cooling with stirring, while keeping the pH between 8.5 and 9.5 with 4N aqueous sodium hydroxide. After stirring for one hour, the mixture was extracted with ethyl acetate (150 ml), washed with brine (50 ml), dried over magnesium sulfate, and concentrated under reduced pressure to give a syrup. The syrup was subjected to a column chromatography on silica gel (60 g) and eluted with a mixture of hexane and ethyl acetate (5:5, V/V) to give 2-[2-(N-benzyl-N-chloroacetylamino)-1-hydroxyethyl]-2-methyl-1,3-dioxolane (5.39 g) as a syrup.

Provenance & Evidence