Reaktion #593191

Reaktionsgleichung

NaOH

POCl3

DMF

1-Ethyl-1H-indole-6-carboxylic acid methyl ester

DMF

→

1-ethyl-3-formyl-1H-indole-6-carboxylic acid methyl ester

Ausbeute 96.0%

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle