3,4-Dimethoxyphenyl methyl ketone → (E)-1-(3,4-dimethoxyphenyl)-3-(dimethylamino)-2-propen-1-one

Participants

Reaction Conditions

Reaction Steps

A mixture of 3,4-dimethoxy acetophenone 11 (5 g, 27.47 mmol) and DMF-DMA (3.9 g, 111.1 mmol) in DMF (10 mL) was heated to 150° C. under an atmosphere of N2. After stirring for 35 h 150° C., the reaction mixture was concentrated in vacuo. The resulting residue was triturated with diethylether and dried under high vacuum to afford compound 12 (5.0 g, 77%) as a yellow solid. TLC Rf=0.5 (CHCl3-MeOH, 9:1); 1H NMR (CDCl3) δ 7.8 (d, J=12.2 Hz, 1H), 7.56-7.51 (m, 3H), 6.86 (d, J=8.1 Hz, 1H), 5.71 (d, J=12.2 Hz, 1H), 3.95 (s, 3H), 3.92 (s, 3H), 3.03 (br, 6H); MS (ES) m/z 236 (M+H+).

Provenance & Evidence