تفاعل #66332

معادلة التفاعل

water

5-bromo-pentene

K2CO3

potassium phthalimide

→

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

المردود 87.9%

المذيبات

DMF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe reaction mixture was cooled to room temperature
2. 2
   استخلاصThe aqueous layer was then extracted with ethyl acetate (2×50 mL)
3. 3
   غسيلthe combined organic layers were washed with 5% aq. NaHCO3 (2×20 mL), brine (30 mL)
4. 4
   تجفيفdried over Na2SO4
5. 5
   ترشيحFiltration and solvent evaporation
6. 6
   أخرىgave an oil, which
7. 7
   أخرىwas purified by flash chromatography (silica gel/hexanes:ethyl acetate 0-35%)

الإجراء التجريبي

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).

المصدر