Ethyl chloroformate → 2-Ethenyl-4,4-dimethyl-1,3-oxazol-5(4H)-one

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Reaction Conditions

Reaction Steps

2-Vinyl-4,4-Dimethylazlactone (VDM) was prepared from N-acryloylmethylalanine (S. M. Heilmann and H. K. Smith II, J. Appl. Polym. Sci., 24, 1551 (1979)) by the Taylor and Platt procedure (L. D. Taylor and T. E. Platt, J. Polym. Sci. Polym. Lett. Ed., 7, 597 (1969)) with ethyl chloroformate as the dehydrating agent. A modified workup procedure was used in which, instead of cooling the filtrate to crystallize the product, the filtrate was concentrated on a rotary evaporator, and the crude product was distilled just above room temperature at 0.5 Torr. Receiving flasks were cooled to −78° C. to collect the product. Typical distilled yields were approximately 80%.

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