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

HRID 502128Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 502128
[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]

Komponenten

5

Edukt 4

HCID 6228Dimethylformamide2×HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 22467242HCID 22467242, Verbindung

Produkt 1

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

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-b470e131cea04679a92a440548ddd12b
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07772271B2

Notizen zur Reaktion

Wird geladen…