Potassium Iodide → methyl 1-(3-methoxypropyl)-1H-indole-6-carboxylate

HRID 922437ノート

反応式

HRID 922437 の反応式
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]([O:12][CH3:13])=[O:11])[CH:8]=2)[CH:3]=[CH:2]1.Br[CH2:15][CH2:16][CH2:17][O:18][CH3:19].[I-].[K+].C(OCC)(=O)C>CN(C)C=O.O>[CH3:19][O:18][CH2:17][CH2:16][CH2:15][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]([O:12][CH3:13])=[O:11])[CH:8]=2)[CH:3]=[CH:2]1

参加物

7

反応物 4

HCID 4875Potassium IodideHCID 8857Ethyl AcetateHCID 5245511-Bromo-3-methoxypropaneHCID 639844Methyl indole-6-carboxylate

生成物 1

HCID 67542758methyl 1-(3-methoxypropyl)-1H-indole-6-carboxylate収率 82.2%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒2 回

実験手順

To a solution of methyl 1H-indole-6-carboxylate (5.0 g) in N,N-dimethylformamide (40 mL) was added dropwise a solution of 1-bromo-3-methoxypropane (5.24 g) in N,N-dimethylformamide (10 mL) under ice-cooling, and then thereto was added potassium iodide (948 mg), and the mixture was stirred at room temperature for 3 hours. To the reaction mixture was sequentially added ethyl acetate and water under ice-cooling, and the organic layer was separated. The organic layer was washed with water twice and saturated saline, dried over sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=9/1→4/1) to give methyl 1-(3-methoxypropyl)-1H-indole-6-carboxylate [REx(6-1)] (5.8 g) as a colorless oil.

後処理

  1. temperaturecooling
  2. temperaturecooling
  3. customthe organic layer was separated
  4. washThe organic layer was washed with water twice
  5. dry with materialsaturated saline, dried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=9/1→4/1)

出典と根拠

ORDレコード
ord-c7a6004ce3b0481282c49eff9bdd8cb4
出典データセット
uspto-grants-2016_03
特許番号
US09278944B2

反応ノート

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