反应 #164452

反应方程式

water

Alcohol

3-Ethoxy-6-(3-hydroxypropyl)cyclohex-2-enone

NEt3

N-methylisatoic anhydride

→

4

收率 45.0%

3-(4-Ethoxy-2-oxocyclohex-3-enyl)propyl 2-(methylamino)benzoate

收率 45.0%

溶剂

DMF

反应条件

后处理

1. 1
   温度After cooling to rt
2. 2
   萃取this mixture was extracted with ethyl acetate (5×50 mL)
3. 3
   洗涤The combined organic layers were washed with brine
4. 4
   干燥dried over Na2SO4
5. 5
   过滤filtered
6. 6
   其他evaporated
7. 7
   其他to give the crude product, which
8. 8
   其他was purified by flash column chromatography

实验过程

Alcohol 3 (180 mg, 0.89 mmol), NEt3 (0.56 mL) and catalytic DMAP were added to a solution of N-methylisatoic anhydride (220 mg, 0.89 mmol) in dry DMF (2.0 mL) at rt. After stirring overnight, the solution was warmed to 65° C. for 3 h. After cooling to rt, water was added and this mixture was extracted with ethyl acetate (5×50 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered, and evaporated to give the crude product, which was purified by flash column chromatography to afford 87.0 mg (45% yield) of 4 as a white solid: 1H NMR (300 MHz, CDCl3) δ 7.85 (1H, m), 7.33 (1H, m), 6.56 (2H, m), 5.27 (1H, s), 4.22 (2H, t, J=5.2 Hz), 3.85 (2H, q, J=7.0 Hz), 2.86 (3H, s), 2.39 (2H, t, J=5.3 Hz), 2.04-1.41 (7H, m), 1.31 (3H, t, J=7.0 Hz); 13C NMR (75 MHz, CDCl3) δ 201.1, 176.8, 168.7, 151.7, 134.7, 131.7, 115.0, 111.3, 110.6, 102.5, 101.9, 64.7, 64.5, 64.3, 44.9, 30.0, 28.2, 26.6, 26.5, 26.4, 14.3; ESI MS m/z 354 (M++Na+).

来源