碳酸钾 → 5-(2-methoxyethoxy)-1H-indole

HRID 41062

反应方程式

HRID 41062 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.[CH3:11][O:12][CH2:13][CH2:14]I.CC(C)=O.C([O-])([O-])=O.[K+].[K+].COCCI>C1(C)C=CC=CC=1.CC(C)=O>[CH3:11][O:12][CH2:13][CH2:14][O:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2

参与物

6

反应物 4

HCID 11430碳酸钾2 次HCID 160545-羟基吲哚HCID 791361-碘-2-甲氧基乙烷HCID 86634331Acetone 2-methoxyethyl iodide

产物 1

HCID 103525375-(2-methoxyethoxy)-1H-indole收率 86.2%

试剂、催化剂与溶剂 1

HCID 20247278Toluene acetone溶剂

实验过程

To a solution of 5-hydroxy-indole (15.2 g, 114 mmol) in 250 ml of dry acetone 2-methoxyethyl iodide (15 ml, 141 mmol, 1.25 equiv) and anhydrous K2CO3 (46.7 g, 338 mmol, 3 equiv) are added and the mixture is refluxed. Additional amounts of 0.5 equiv of 2-methoxyethyl iodide and K2CO3 are added each day. After 6 days TLC (toluene-acetone, 9:1) indicates the absence of starting material. The solid is removed by filtration, and the solvent is evaporated. The residue is taken up in dichloromethane (800 ml) and the solution is washed with 2 M aqueous HCl, 10% aqueous NaHCO3, and water. The organic layer is dried and concentrated. Column chromatography (toluene-acetone, 9:1) provides 5-(2-methoxyethoxy)-1H-indole (18.8 g, 86%). M.p. 58-60° C. (from ethyl acetate-light petroleum).

后处理

  1. temperaturethe mixture is refluxed
  2. customThe solid is removed by filtration
  3. customthe solvent is evaporated
  4. washthe solution is washed with 2 M aqueous HCl, 10% aqueous NaHCO3, and water
  5. customThe organic layer is dried
  6. concentrationconcentrated

来源与证据

ORD记录
ord-a397b75c02ed433587cf9bf2dbd0b0f4
来源数据集
uspto-grants-2013_09
专利号
US08530493B2

关联笔记

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