Diethyl (ethoxymethylene)malonate → diethyl N-(3-oxo-1-cyclohexen-1-yl)-aminomethylenemalonate

Participants

Reaction Steps

A mixture of 11.1 g of 3-amino-2-cyclohexenone, 24.2 g of ethoxymethylenemalonic acid diethyl ester, and 0.12 g of p-toluenesulfonic acid was heated on an oil bath at 120°-130° C. for 2 hours. Using column chromatography, the reaction product was purified to obtain a yield of 19.8 g of N-(3-oxo-1-cyclohexen-1-yl)aminomethylenemalonic acid diethyl ester in the form of a pale-yellow viscous oil. The n.m.r. spectrum (d6 -DMSO, 60Mc, TMS) of this compound had signals at δ values of 1.24 (3H, t, J=7 Hz), 1.26 (3H, t, J=7 Hz), 1.7-2.75 (6H, m), 4.10 (2H, q, J=7 Hz), 4.18 (2H, q, J=7 Hz), 5.75 (H, s), 8.05 (1H, d, J=13.8 Hz), and 10.2 (1H, d, J=13.8 Hz).

Provenance & Evidence