Potassium Carbonate → 5-(2-methoxyethoxy)-1H-indole

HRID 41062

反応式

HRID 41062 の反応式
[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

参加物

6

反応物 4

HCID 11430Potassium Carbonate2 回HCID 160545-HydroxyindoleHCID 791361-Iodo-2-methoxyethaneHCID 86634331Acetone 2-methoxyethyl iodide

生成物 1

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

試薬・触媒・溶媒 1

HCID 20247278Toluene acetone溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-a397b75c02ed433587cf9bf2dbd0b0f4
出典データセット
uspto-grants-2013_09
特許番号
US08530493B2

関連ノート

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