Hydrochloric Acid → (E)-N-(4-(2-(dimethylamino)ethoxy)phenyl)-2-(4-hydroxyphenyl)-3-phenylpent-2-enamide

Participants

Reaction Steps

Method A; To a suspension of 4 (1.39 g, 2.93 mmol) in MeOH (4 ml) was added a solution of 3N HCl in AcOEt (10 ml) under ice cooling, and the mixture was stirred at room temperature for 2 h. A solution of NaHCO3 (2.8 g) in H2O was poured into the reaction mixture under ice cooling, and the whole was extracted with AcOEt and a little MeOH. The organic layer was washed with brine, dried over Na2SO4, and then concentrated. The residual solid was triturated with Et2O to give 5 (91%). 5: colorless powder; 1H-NMR (CD3OD) δ 0.97 (3H, t, J=7.4 Hz), 2.38 (6H, s), 2.65 (2H, q, J=7.4 Hz), 2.82 (2H, t, J=5.4 Hz), 4.11 (2H, t, J=5.74 Hz), 6.50 (2H, d, J=8.8 Hz), 6.92 (2H, d, J=8.8 Hz), 6.94 (2H, d, J=9.2 Hz) 7.11-7.25 (5H, m), 7.53 (2H, d, J=9.1 Hz). 13C-NMR (CD3OD) δ 13.21, 30.40, 45.76, 59.09, 66.74, 115.69, 115.75, 123.42, 127.91, 129.10, 129.31, 130.42, 131 0.78,

Provenance & Evidence