Water → 1-ethyl-1H-imidazole-5-carbaldehyde

HRID 1186369Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1186369
[NH:1]1[C:5]([CH:6]=[O:7])=[CH:4][N:3]=[CH:2]1.C(=O)([O-])[O-].[K+].[K+].[CH2:14](I)[CH3:15].O>CN(C)C=O.C(OCC)(=O)C>[CH2:14]([N:1]1[C:5]([CH:6]=[O:7])=[CH:4][N:3]=[CH:2]1)[CH3:15].[CH2:14]([N:3]1[CH:4]=[C:5]([CH:6]=[O:7])[N:1]=[CH:2]1)[CH3:15]

Komponenten

8

Edukt 4

HCID 962WaterHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 764281H-Imidazole-4-carbaldehyde

Produkt 2

HCID 31596721-ethyl-1H-imidazole-5-carbaldehydeAusbeute 30 %HCID 135098721-Ethyl-1H-imidazole-4-carbaldehydeAusbeute 9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

1H-Imidazole-5-carbaldehyde (300 mg, 3.12 mmol) was dissolved in N,N-dimethylformamide (4 mL). To this, potassium carbonate (862 mg, 6.24 mmol) and ethyl iodide (0.275 mL, 3.43 mmol) were added at room temperature and the mixture was stirred at the same temperature for 1.5 hours. After water was added to the reaction mixture, extraction with ethyl acetate was performed, followed by washing with brine and drying over anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure, and the residue was purified by preparative thin-layer chromatography (chloroform/methanol=20/1) to give 1-ethyl-1H-imidazole-5-carbaldehyde (115 mg, yield: 30%) and 1-ethyl-1H-imidazole-4-carbaldehyde (36 mg, yield: 9%). 1-ethyl-1H-imidazole-5-carbaldehyde

Aufarbeitung

  1. washby washing with brine
  2. dry with materialdrying over anhydrous sodium sulfate
  3. customThe solvent was evaporated off under reduced pressure
  4. customthe residue was purified by preparative thin-layer chromatography (chloroform/methanol=20/1)

Quellen und Nachweise

ORD-Eintrag
ord-4e89b32c2f034fbdb8b166bf66a9ba3b
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08673908B2

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