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

HRID 68218

反応式

HRID 68218 の反応式
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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

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).

後処理

  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%)

出典と根拠

ORDレコード
ord-968a86666c514b66ad2f8f26e08fb3e7
出典データセット
uspto-grants-2014_09
特許番号
US08822424B2

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