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

HRID 68218

반응식

HRID 68218 반응식
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]

참가 물질

6

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 707041-Pentene, 5-bromo-HCID 24194345Phthalimide potassium salt

생성물 1

HCID 3394342-(pent-4-en-1-yl)-2,3-dihydro-1H-isoindole-1,3-dione수율 87.9%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

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, 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).

후처리

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

출처 및 근거

ORD 기록
ord-968a86666c514b66ad2f8f26e08fb3e7
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822424B2

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