聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯] → 2-pent-4-en-1-yl-1H-isoindole-1,3(2H)-dione

HRID 38121笔记

反应方程式

HRID 38121 反应方程式
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]

参与物

6

反应物 4

HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]HCID 11430碳酸钾HCID 707045-溴-1-戊烯HCID 24194345邻苯二甲酰亚胺钾盐

产物 1

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

试剂、催化剂与溶剂 1

HCID 6228N,N-二甲基甲酰胺溶剂

反应条件

温度
100 °C

实验过程

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).

后处理

  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%)

来源与证据

ORD记录
ord-562ad9d5744848ac81f7bdd9619a6887
来源数据集
uspto-grants-2013_09
专利号
US08524689B2

反应笔记

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