Ethyl allyl(2,2-dimethoxyethyl)carbamate → Ethyl allyl(2-oxoethyl)carbamate

Participants

Reaction Steps

A solution of ethyl N-(2,2-dimethoxyethyl)-N-prop-2-enylcarbamate (Intermediate 42, 1218 g, 2.79 mol) in HCOOH (4.2 L) was refluxed for 0.5 h. Then crushed ice was added to quench the reaction, the mixture was extracted with CH2Cl2 (2 L×3). The combined organic solutions were washed with sat. NaHCO3 (3 L), dried (Na2SO4) and concentrated in vacuo to give the title compound (480 g, 50%) as yellow oil; 1H NMR: (CDCl3) 1.15-1.32 (3H, m), 3.89-4.00 (4H, m), 4.07-4.16 (2H, m), 5.10 (2H, m), 5.73 (1H, m), 9.53 (1H, s).

Provenance & Evidence