反応 #10811

反応方程式

4-acetyl-benzamide

2-(2-morpholin-4-yl-ethoxy)-4-methoxy-5-thiophen-2-yl-benzaldehyde

lithium methoxide

→

title compound

収率 57.1%

4-{3E-[4-Methoxy-2-(2-morpholin-4-yl-ethoxy)-5-thiophen-2-yl-phenyl]-acryloyl}-benzamide

収率 57.1%

溶媒

DMF

methanol

反応条件

後処理

1. 1
   その他The reaction was quenched with water after 2 hours
2. 2
   抽出The aqueous solution was extracted with ethyl acetate
3. 3
   抽出The combined extract
4. 4
   洗浄was washed with NaHCO3, NH4Cl, brine
5. 5
   乾燥dried (Na2SO4)
6. 6
   濃縮concentrated
7. 7
   workup.STIRRINGThe residue was stirred in ethanol overnight

実験手順

To a solution of 4-acetyl-benzamide (Ex-92A, 0.25 g, 1.53 mmol) and 2-(2-morpholin-4-yl-ethoxy)-4-methoxy-5-thiophen-2-yl-benzaldehyde (Ex-60A, 0.53 g, 1.53 mmol) in DMF (7 mL) and methanol (3 mL) was added lithium methoxide. The solution was allowed to stir at ambient temperature. The reaction was quenched with water after 2 hours. The aqueous solution was extracted with ethyl acetate. The combined extract was washed with NaHCO3, NH4Cl, brine, dried (Na2SO4) and concentrated. The residue was stirred in ethanol overnight to afford the title compound as a yellow solid (0.43 g, 57%), mp 183–184° C. 1H-NMR (CDCl3) δ 8.09–8.04 (m, 3H), 7.93 (d, J=8.3 Hz, 2H), 7.87 (s, 1H), 7.57 (d, J=15.7 Hz, 1H), 7.42 (d, J=3.9 Hz, 1H), 7.32 (d, 4.4 Hz, 1H), 7.11–7.08 (m, 1H), 6.55 (s, 1H), 6.25 (bs, 1H), 5.75 (bs, 1H), 4.25 (t, J=5.9 Hz, 2H), 3.98 (s, 3H), 3.71 (t, J=4.2 Hz, 4H), 2.92 (t, J=5.7 Hz, 2H), 2.59 (t, J=4.6 Hz, 4H). MS m/z=493 ([M+H]+, 100%).

出典