反応 #164452

反応方程式

water

Alcohol

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

NEt3

N-methylisatoic anhydride

→

4

収率 45.0%

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

収率 45.0%

溶媒

DMF

反応条件

後処理

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

実験手順

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+).

出典