Water → 2-(pent-4-en-1-yl)-2,3-dihydro-1H-isoindole-1,3-dione

HRID 38121

Reaction equation

Br[CH2:2][CH2:3][CH2:4][CH:5]=[CH2:6].C([O-])([O-])=O.[K+].[K+].[C:13]1(=[O:23])[NH:17][C:16](=[O:18])[C:15]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:14]12.[K].O>CN(C=O)C>[CH2:2]([N:17]1[C:13](=[O:23])[C:14]2[C:15](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:16]1=[O:18])[CH2:3][CH2:4][CH:5]=[CH2:6]

Participants

Conditions

Temperature: 100 °C

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, 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).

Workup

temperatureThe reaction mixture was cooled to room temperature
extractionThe aqueous layer was then extracted with ethyl acetate (2×50 mL)
washthe combined organic layers were washed with 5% aq. NaHCO3 (2×20 mL), brine (30 mL)
dry with materialdried over Na2SO4
filtrationFiltration and solvent evaporation
customgave an oil, which
customwas purified by flash chromatography (silica gel/hexanes:ethyl acetate 0-35%)

Sources & evidence

ORD record: ord-562ad9d5744848ac81f7bdd9619a6887
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08524689B2

Linked notes

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