Imidazole → 3-(1H-Imidazol-1-yl)benzenemethanol

HRID 2242360Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2242360
I[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][OH:6].[NH:10]1[CH:14]=[CH:13][N:12]=[CH:11]1.C(=O)([O-])[O-].[K+].[K+].[F-].[K+]>CN(C=O)C.[Cu]>[N:10]1([C:2]2[CH:3]=[C:4]([CH2:5][OH:6])[CH:7]=[CH:8][CH:9]=2)[CH:14]=[CH:13][N:12]=[CH:11]1

Komponenten

7

Edukt 4

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 423003-Iodobenzyl alcoholHCID 522689Potassium Fluoride

Produkt 1

HCID 197444983-(1H-Imidazol-1-yl)benzenemethanolAusbeute 86,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23978CopperKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

3-Iodobenzylalcohol (5.17 g, 21.0 mmol), imidazole (1.73 g, 25.2 mmol), potassium carbonate (3.78 g, 27.3 mmol), copper (0) powder (275 mg, 4.33 mmol) and potassium fluoride (260 mg, 4.44 mmol) in DMF (30 ml) were refluxed at 175° C. for 6 h. The reaction was filtered, the solid washed with DCM and washing and filtrate concentrated. Purification by silica chromatography using DCM followed by DCM:MeOH (15:1 then 10:1) yielded (3-imidazol-1-yl-phenyl)-methanol as an orange oil (3.17 g, 72%).

Aufarbeitung

  1. filtrationThe reaction was filtered
  2. washthe solid washed with DCM
  3. washwashing
  4. concentrationfiltrate concentrated
  5. customPurification by silica chromatography

Quellen und Nachweise

ORD-Eintrag
ord-39a53722e6264b1cbe7615305a149641
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07671080B2

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