A new-synthetic method for 4-chloromethyl-5-methyl-1, 3-dioxol-2-one (1c), which is useful for preparing prodrugs, has been developed. Ene-chlorination of 4, 5-dimethyl-1, 3-dioxol-2-one (2) with chlorine or sulfuryl chloride afforded 4-chloro-4-methyl-5-methylene-1, 3-dioxolan-2-one (3) in good yield. Compound 3 underwent allylic rearrangement to afford 1c quantiatively. The overall yield of 1c from 2 was approximately 80%.
