Dimethyl Sulfoxide → 1-Allyloxycarbonyl-3-(2-methyl-3-oxo-1-butenyl)azetidine

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Reaction Steps

To a solution of oxalyl chloride (6.3 g) in methylene chloride (85 ml) was added dimethyl sulfoxide (3.87 g) at -60° C. and stirred was stirred for 15 minutes. A solution of 1-allyloxycarbonyl-3-hydroxymethylazetidine (6.8 g) in methylene chloride (21 ml) was then added thereto and the mixture was stirred at -60° C. for 30 minutes. Triethylamine (20 g) was dropwise added thereto. To the mixture was added water (50 ml) and organic layer was separated washed with water, dried over magnesium sulfate, evaporated and coevaporated with benzene to give an oily residue. The residue was dissolved in methylene chloride (160 ml) and 3-triphenylphosphoranylidenebutan-2-one (11.8 g) was added thereto and the mixture was stirred overnight at room temperature. The evaporated residue was triturated with ethyl acetate and the insoluble material was filtered. The filtrate was applied on silica gel column using a mixture of n-hexane and ethyl acetate. The main fractions were evaporated to give 1-allyloxycarbonyl-3-(2-methyl-3-oxo-1-butenyl)azetidine (7.06 g).

Provenance & Evidence