1H-Imidazole-5-methanol, 2-butyl-1-[(2-chlorophenyl)methyl]- → 1H-Imidazole-5-carboxaldehyde, 2-butyl-1-[(2-chlorophenyl)methyl]-

HRID 36971

Reaktionsgleichung

Reaktionsgleichung von HRID 36971
[CH2:1]([C:5]1[N:6]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:19])[C:7]([CH2:10][OH:11])=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4]>C1(C)C=CC=CC=1.C(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH2:1]([C:5]1[N:6]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:19])[C:7]([CH:10]=[O:11])=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4]

Komponenten

5

Edukt 1

HCID 100164181H-Imidazole-5-methanol, 2-butyl-1-[(2-chlorophenyl)methyl]-

Produkt 1

HCID 101075301H-Imidazole-5-carboxaldehyde, 2-butyl-1-[(2-chlorophenyl)methyl]-Ausbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418406HCID 178418406, VerbindungKatalysatorHCID 1140TolueneLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 2-n-butyl-1-(2-chlorophenyl)methyl-5-hydroxymethyl-1H-imidazole (5.4 g, 0.0194 mol) in toluene (25 mL) was added to a suspension of activated manganese dioxide (27 g) in methylene chloride (325 mL). The suspension was stirred at room temperature for 17 hours. The solids were filtered and the filtrate concentrated and flash chromatographed over silica gel with 6:4 hexane/ethyl acetate to afford 4.16 g (78%) of 2-n-butyl-1-(2-chlorophenyl)methyl-1H-imidazol-5-carboxaldehyde, as an oil. NMR and IR were consistent with the structure.

Aufarbeitung

  1. filtrationThe solids were filtered
  2. concentrationthe filtrate concentrated
  3. customflash chromatographed over silica gel with 6:4 hexane/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-e86501f95243498d820ce062c8d77e2d
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05418250

Verknüpfte Notizen

Wird geladen…