(E)-3-(dimethylamino)-1-(furan-2-yl)prop-2-en-1-one synthesis

Yield:17168-45-5 97%

Reaction Conditions:

at 100; for 9 h;

Steps:

14 Reference Example 14: 3-(Dimethylamino)-1-(2-furyl)-2-propen-1-one

A mixture of 2-acetylfuran (25.0 g, 0.227 mmol) and N,N-dimethylformamide dimethylacetal (40 ml) was stirred at 100°C for 9 hours. After cooling as it was, the reaction mixture was concentrated. To the residue were added diethyl ether and hexane. The resulting solid was collected by filtration and washed with hexane, to give the title compound (36.5 g, 97%) as a brown solid.1H NMR (400 MHz, DMSO-d6) δ ppm; 2.88 (3H, br s), 3.14 (3H, br s), 5.65 (1H, d, J= 12.6 Hz), 6.60 (1H, dd, J=2.0, 3.4 Hz), 7.10 (1H, dd, J = 0.8, 3.4 Hz), 7.68 (1H, d, J = 12.6 Hz), 7.79 (1H, dd, J = 0.8, 2.0 Hz).

References:

EP1439175,2004,A1 Location in patent:Page 45-46