1H-Indole-3-propanoic acid → Methyl 3-(1H-indol-3-yl)propanoate

HRID 1417456

反応式

HRID 1417456 の反応式
[C:1](=O)([O-])[O-].[K+].[K+].[NH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([CH2:16][CH2:17][C:18]([OH:20])=[O:19])=[CH:8]1.CI>CN(C)C=O>[NH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([CH2:16][CH2:17][C:18]([O:20][CH3:1])=[O:19])=[CH:8]1

参加物

5

反応物 3

HCID 37441H-Indole-3-propanoic acidHCID 6328Methyl iodideHCID 11430Potassium Carbonate

生成物 1

HCID 21711Methyl 3-(1H-indol-3-yl)propanoate収率 96.9%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

36.2 g of powdered potassium carbonate was added, with ice-cooling, to a solution of 24.8 g of 3-(indol-3-yl)propionic acid in 500 ml of N,N-dimethylformamide, followed by the addition of a solution of 10.2 ml methyl iodide in 50 ml of N,N-dimethylformamide. The reaction mixture was then warmed to room temperature and stirred for 3 hours. After this time, ice water was added to the reaction mixture, and the aqueous layer was extracted with ethyl acetate. The organic extract was then washed with water, dried over anhydrous magnesium sulfate and concentrated by evaporation under reduced pressure. The resulting residue was subjected to column chromatography using 500 g of silica gel with a 4:1 v/v mixture of hexane and ethyl acetate as the eluent, to yield 25.8 g of the title compound as an amorphous solid.

後処理

  1. extractionthe aqueous layer was extracted with ethyl acetate
  2. extractionThe organic extract
  3. washwas then washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated by evaporation under reduced pressure
  6. additionwith a 4:1 v/v mixture of hexane and ethyl acetate as the eluent

出典と根拠

ORDレコード
ord-6e4421d7733742f59e8f12b8135a2a1f
出典データセット
uspto-grants-1999_03
特許番号
US05877199

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