반응 #66332

반응 방정식

water

5-bromo-pentene

K2CO3

potassium phthalimide

→

2-(pent-4-enyl)-isoindoline-1,3-dione

수율 87.9%

용매

DMF

반응 조건

후처리

1. 1
   온도The reaction mixture was cooled to room temperature
2. 2
   추출The aqueous layer was then extracted with ethyl acetate (2×50 mL)
3. 3
   세척the combined organic layers were washed with 5% aq. NaHCO3 (2×20 mL), brine (30 mL)
4. 4
   건조dried over Na2SO4
5. 5
   여과Filtration and solvent evaporation
6. 6
   기타gave an oil, which
7. 7
   기타was purified by flash chromatography (silica gel/hexanes:ethyl acetate 0-35%)

실험 절차

To a stirring solution of 5-bromo-pentene (6.0 g, 0.040 mol) in DMF (30 mL) was added K2CO3 (4.7 g, 0.034 mol) and potassium phthalimide (6.21 g, 0.033 mmol) and the reaction mixture was heated at 100° C. for 1 hr. The reaction mixture was cooled to room temperature, and water (50 mL) was added. The aqueous layer was then extracted with ethyl acetate (2×50 mL), and the combined organic layers were washed with 5% aq. NaHCO3 (2×20 mL), brine (30 mL) and dried over Na2SO4. Filtration and solvent evaporation gave an oil, which was purified by flash chromatography (silica gel/hexanes:ethyl acetate 0-35%) to yield the desired 2-(pent-4-enyl)-isoindoline-1,3-dione as a solid (6.36 g, 0.029 mmol, 72.5% yield): MS m/e [M+H]+ calcd 216.1, found 216.1; NMR (250 MHz, DMSO-d6) δ 7.79-7.95 (m, 4 H), 5.70-5.91 (m, 1 H), 4.90-5.11 (m, 2 H), 3.58 (t, 2 H), 1.98-2.10 (m, 2 H), 1.59-1.78 (m, 2 H).

출처