Abstract We report a metal-free synthesis of N-alkyl-4-vinyl oxazolidinones. In the presence of sodium hydride, 4-chloro-1-hydroxy-2-butene reacts efficiently with N-alkyl carbamoylimidazoles to give carbamate intermediates, which undergo a subsequent SN2′ ring closure, providing the N-alkyl-4-vinyl oxazolidinones in high yield on a gram scale.
Punjabi et al. (Tue,) studied this question.