Ethylene Glycol → 2-[2-(N-allyloxycarbonyl-N-benzylamino)-1-hydroxyethyl]-2-methyl-1,3-dioxolane

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Reaction Steps

Mercury(II) sulfate (3.55 g) was added to a solution of 1-(N-allyloxycarbonyl-N-benzylamino)-4-trimethylsilyl-3-butyn-2-ol (19.75 g) in a mixture of sulfuric acid (0.15 ml), ethylene glycol (60 ml), and tetrahydrofuran (120 ml). The mixture was stirred at 30°~40° C. for 35 hours. Sodium hydrogen carbonate (1 g) was added to the mixture and the mixture was stirred at 30°~40° C. for one hour. An insoluble material was filtered off and the filtrate was concentrated under reduced pressure to give a syrup. A solution of the syrup in ethyl acetate (250 ml) was washed with water (150 ml), dried over magnesium sulfate, and concentrated under reduced pressure to give an oil. The oil was subjected to a column chromatography on silica gel (400 g) and eluted with a mixture of hexane and ethyl acetate (5:5, V/V) to give 2-[2-(N-allyloxycarbonyl-N-benzylamino)-1-hydroxyethyl]-2-methyl-1,3-dioxolane (11.6 g) as a syrup.

Provenance & Evidence