Dimethylformamide → Methyl 1-ethyl-3-formyl-1H-indole-6-carboxylate

HRID 502128ノート

反応式

HRID 502128 の反応式
[CH3:1][O:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([CH:9]=[CH:10][N:11]2[CH2:14][CH3:15])=[CH:7][CH:6]=1)=[O:4].O=P(Cl)(Cl)Cl.[OH-].[Na+].CN([CH:26]=[O:27])C>>[CH3:1][O:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([C:9]([CH:26]=[O:27])=[CH:10][N:11]2[CH2:14][CH3:15])=[CH:7][CH:6]=1)=[O:4]

参加物

5

反応物 4

HCID 6228Dimethylformamide2 回HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 22467242HCID 22467242、化合物

生成物 1

HCID 59425156Methyl 1-ethyl-3-formyl-1H-indole-6-carboxylate収率 96%

実験手順

1-Ethyl-1H-indole-6-carboxylic acid methyl ester (900 mg, 4.45 mmol) is dissolved in DMF (3.3 mL). This is added dropwise to an ice-cold solution of POCl3 (430 μL, 4.5 mmol) in DMF (1.5 mL). The reaction mixture is stirred at room temperature for 90 minutes. The reaction mixture is then treated with 6N NaOH (3.5 ml). The mixture is then partitioned between H2O and ethyl acetate. Purification by silica gel chromatography (5-10% EtOAc/CH2Cl2) yields 1-ethyl-3-formyl-1H-indole-6-carboxylic acid methyl ester (985 mg, 96%) as a white solid.

後処理

  1. customThe mixture is then partitioned between H2O and ethyl acetate
  2. customPurification by silica gel chromatography (5-10% EtOAc/CH2Cl2)

出典と根拠

ORDレコード
ord-b470e131cea04679a92a440548ddd12b
出典データセット
uspto-grants-2010_08
特許番号
US07772271B2

反応ノート

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