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

HRID 260737

Reaction equation

HRID 260737 reaction equation
[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]>C(Cl)Cl>[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]

Participants

3

Reactant 1

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-n-butyl-1-(2-chlorophenyl)methyl-5-hydroxymethyl-1H-imidazole (5.4 g, 0.0194 mol) in methylene chloride (25 mL) was added to a suspension of activated maganese 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.

Workup

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

Sources & evidence

ORD record
ord-480aa838d56947449c0081815df89371
Source dataset
uspto-grants-1996_06
Patent number
US05530017

Linked notes

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