[C:1]([O:6][CH2:7][CH2:8][OH:9])(=[O:5])[C:2]([CH3:4])=[CH2:3].CN(C)C.Cl[C:15]([O:17][CH2:18][C:19]#[CH:20])=[O:16].C(Cl)Cl.O>C(Cl)Cl>[C:1]([O:6][CH2:7][CH2:8][O:9][C:15]([O:17][CH2:18][C:19]#[CH:20])=[O:16])(=[O:5])[C:2]([CH3:4])=[CH2:3]A flask equipped with a stirrer, thermometer, nitrogen gas tube and reflux condenser was charged with 13.0 g of 2-hydroxyethyl methacrylate and 11.5 g of trimethylamine in 50.0 g of methylene chloride. To the flask was added 13.0 g of propargyl chloroformate dropwise over one hour. The mixture was allowed to react for 6 hours at 30° C. After the reaction, the mixture was treated with methylene chloride-water mixture. The organic phase was separated and dried over magnesium sulfate. After filtering, the filtrate was evaporated in a rotary evaporator. The resulting residue was applied on a 200 mesh silica gel column and developed with ethyl acetate-hexane mixture. The title compound was obtained as colorless liquid. Yield was 73.6% of theory.
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