반응 #164452

반응 방정식

water

Alcohol

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

NEt3

N-methylisatoic anhydride

→

4

수율 45.0%

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

수율 45.0%

용매

DMF

반응 조건

후처리

1. 1
   온도After cooling to rt
2. 2
   추출this mixture was extracted with ethyl acetate (5×50 mL)
3. 3
   세척The combined organic layers were washed with brine
4. 4
   건조dried over Na2SO4
5. 5
   여과filtered
6. 6
   기타evaporated
7. 7
   기타to give the crude product, which
8. 8
   기타was purified by flash column chromatography

실험 절차

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+).

출처