碘乙烷 → 5-乙氧基吲哚

HRID 41061

反应方程式

HRID 41061 反应方程式
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.C([O-])([O-])=O.[K+].[K+].I[CH2:18][CH3:19].ClCCl.CO>CC(C)=O>[CH2:18]([O:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2)[CH3:19]

参与物

6

反应物 4

HCID 6340碘乙烷HCID 11430碳酸钾HCID 160545-羟基吲哚2 次HCID 21226129Dichloromethane methanol

产物 1

HCID 47776675-乙氧基吲哚收率 90%

试剂、催化剂与溶剂 1

HCID 180丙酮溶剂

反应条件

温度
50 °C

实验过程

A mixture of commercially available 5-hydroxy-indole (18 g, 13.5 mmol), anhydrous K2CO3 (93.5 g, 5 equiv) and iodoethane (40.5 ml, 3.75 equiv) in acetone (180 mL) is stirred at 50° C. under argon. When TLC (dichloromethane-methanol, 95:5) indicates the disappearance of 5-hydroxy-indole (4 days), the mixture is filtered, the solid is washed with acetone, then the filtrate is concentrated to give 17.67 g (90%) of the title compound, which is sufficiently pure to be used in the next step. M.p. 144-146° C. (from ethanol).

后处理

  1. filtrationthe mixture is filtered
  2. washthe solid is washed with acetone
  3. concentrationthe filtrate is concentrated

来源与证据

ORD记录
ord-7954df6899c24f36acc08db5c4700c76
来源数据集
uspto-grants-2013_09
专利号
US08530493B2

关联笔记

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