2,2,2-Trichloroethyl (1E)-buta-1,3-dien-1-ylcarbamate

synthetischeThe synthesis of trans-1,3-butadienecarbamates utilizes a modified Curtius rearragement. In the synthesis of 2,2,2-trichloroethyl trans-1,3-butadiene-1-carbamate, Malonic Acid and Acrolein were condensed in pyridine to obtain trans-2,4- pentadienoic acid in 44-51% yield (eq 1). This compound, which may be stored in a freezer for several months, was treated with Ethyl Chloroformate and the resulting mixed anhydride transformed into the azide derivative. Due to the explosive nature, the azide was not isolated but immediately added to a refluxing solution of 2,2,2-Trichloroethanol in toluene. Purification by silica gel column chromatography (hexane-ethyl acetate = 9:1) then afforded the title compound.