2-Propenoic acid, 2-[(methoxycarbonyl)amino]-, methyl ester → Methyl alpha-isocyanatoacrylate

Participants

Reaction Conditions

Reaction Steps

The apparatus and procedure used in Example 6 are repeated except that the tube is filled with silica-alumina (Strem, 87% silica, 52.39 g after drying). A solution of methyl alpha-(methoxycarbonylamino)-acrylate (5.86 g, 0.37 mmol) in 10 ml toluene is passed down the column. Both traps are cooled to -78° C., and the contents are combined for analysis. 1H NMR of the reaction products (14.2 g including toluene) indicated a 90% conversion of starting material and a 50% yield of isocyanate.

Provenance & Evidence