Water → 1,6-Dimethyl-1H-indole-3-carbaldehyde

HRID 442744

Reaktionsgleichung

Reaktionsgleichung von HRID 442744
[CH3:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:11]=[O:12])=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[H-].[Na+].[CH3:15]I.O>CN(C=O)C>[CH3:15][N:8]1[C:9]2[C:5](=[CH:4][CH:3]=[C:2]([CH3:1])[CH:10]=2)[C:6]([CH:11]=[O:12])=[CH:7]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 47779026-Methylindole-3-carboxaldehyde

Produkt 1

HCID 225937461,6-Dimethyl-1H-indole-3-carbaldehydeAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of the known 6-methyl-1H-indole-3-carboxaldehyde (5 g, 31 mm) in DMF (100 mL) was cooled to 0° C. and treated with NaH (38 mm), and stirred at 0° C. for 3 hours. After treatment with CH3I (2.35 mL, 38 mm), the mixture was allowed to warm to room temperature overnight. The mixture was poured into H2O(500 mL) and extracted with ethylacetate (EtOAc) (200 mL×3). The combined organic layers were dried over MgSO4, filtered and evaporated. Purification by flash column chromatography afforded 1,6-dimethyl-1H-indole-3-carboxaldehyde (5.2 g, 97%).

Aufarbeitung

  1. temperatureto warm to room temperature overnight
  2. extractionextracted with ethylacetate (EtOAc) (200 mL×3)
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customPurification by flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-56cb28cf919340c083e1a725acc2a2fc
Quelldatensatz
uspto-grants-1999_04
Patentnummer
US05891901

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