Dimethylamine → 1-(4-Benzyloxyphenyl)-1-(dimethylamino)-2-(4-methoxyphenyl)ethylene

Participants

Reaction Conditions

Reaction Steps

Dimethylamine (55 mL, 0.15 mol) in 100 mL of toluene was added over ten min at 0°-5° C. to a 600 mL toluene suspension of 1-(4-benzyloxyphenyl)-2-(4-methoxyphenyl)ethan-l-one (50 g, 0.15 mol), then stirred 15 min at 0° C. A 50 mL toluene solution of TiCl4 (9.8 mL, 0.09 mol) was added dropwise over 1 h to the reaction mixture, keeping the temperature below 5° C. The brown suspension was stirred 16 h at rt then filtered through Hyflo Super Cel to give a yellow filtrate. Two Et2O washes of the filter bed were combined with the filtrate and the solution was concentrated to a thick amber oil. The oil was triturated with Et2O/ pet. ether and filtered to give 41 g (77%) of yellow solid: mp 60° C.; 1H NMR (CDCl3) d 2.64 (s, 6H, NMe2), 3.71 (s, 3H, OCH3), 5.07 (s, 2H, OCH2), 5.42 (s, 1H, =CH), 6.57-6.60 (d, 2H, J=9 Hz, ArH), 6.67-6.70 (d, 2H, J=9 Hz, ArH), 6.86-6.89 (d, 2H, J=9 Hz, ArH), 6.90-6.93 (d, 2H, J=9 Hz, ArH), 7.18-7.21 (d, 2H, J=9 Hz, ArH), 7.40-7.45 (m, 5H, ArH); MS(FD) 360[M+1]+Anal. Calcd for C24H25NO2 : C, 80.19; H, 7.01; N, 3.90. Found: C, 80.41; H, 7.12; N, 4.09.

Provenance & Evidence