聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯] → 7-(3-chloropropoxy)-1H-indole

HRID 235406

反应方程式

HRID 235406 反应方程式
[H-].[Na+].[OH:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][CH:10]=[CH:9]2.Br[CH2:14][CH2:15][CH2:16][Cl:17].O>CN(C)C=O>[Cl:17][CH2:16][CH2:15][CH2:14][O:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][CH:10]=[CH:9]2

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 80061-溴-3-氯丙烷HCID 24758氢化钠HCID 27376517-羟基吲哚

产物 1

HCID 153849647-(3-chloropropoxy)-1H-indole

试剂、催化剂与溶剂 1

HCID 6228N,N-二甲基甲酰胺溶剂3 次

实验过程

To a stirred suspension of sodium hydride (0.8 g, 17 mmol of a 50% oil dispersion) in dimethylformamide (20 ml), under nitrogen, was added dropwise 7-hydroxyindole (2.1 g, 15.7 mmol) in dimethylformamide (20 ml). After complete addition, the reaction was stirred at ambient temperature for 0.5 hour and then cooled to 15° C. To this cooled solution was added, dropwise, 1-bromo-3-chloropropane (2.5 g, 15.7 mmol) in dimethylformamide (5 ml). The reaction was then stirred at ambient temperature for 16 hours. The reaction was poured into water, and the aqueous suspension extracted with ethyl acetate. The ethyl acetate was washed with water, dried (MgSO4), and the solvent was concentrated to afford a dark brown oil. Following flash chromatography on silica gel, 7-(3-chloropropoxy)indole was obtained as a colorless oil, 1.0 g.

后处理

  1. additionAfter complete addition
  2. temperaturecooled to 15° C
  3. additionTo this cooled solution was added
  4. stirringThe reaction was then stirred at ambient temperature for 16 hours
  5. extractionthe aqueous suspension extracted with ethyl acetate
  6. washThe ethyl acetate was washed with water
  7. dry with materialdried (MgSO4)
  8. concentrationthe solvent was concentrated
  9. customto afford a dark brown oil

来源与证据

ORD记录
ord-d45e6cffcb844f18b8d7ab88dfa912d2
来源数据集
uspto-grants-1997_01
专利号
US05597842

关联笔记

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