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

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.

1. temperaturecooling
2. stirringAfter stirring for one hour
3. extractionthe mixture was extracted with ethyl acetate (150 ml)
4. washwashed with brine (50 ml)
5. dry with materialdried over magnesium sulfate
6. concentrationconcentrated under reduced pressure
7. customto give a syrup
8. washeluted with a mixture of hexane and ethyl acetate (5:5, V/V)

ORD record

ord-fd1bf3d9b5564b71b072ccf8e17c2fb0

Source dataset

uspto-grants-1992_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05102877