Reaction #155400

Reaction equation

water

5-bromo-pentene

K2CO3

potassium phthalimide

→

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

Yield 87.9%

Solvents

DMF

Conditions

Workup

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

Procedure

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).

Source