Reacción #155400

Ecuación de reacción

water

5-bromo-pentene

K2CO3

potassium phthalimide

→

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

Rendimiento 87.9%

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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, 4H), 5.70-5.91 (m, 1H), 4.90-5.11 (m, 2H), 3.58 (t, 2H), 1.98-2.10 (m, 2H), 1.59-1.78 (m, 2H).

Fuente