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

HRID 1757180Notes

Reaction equation

HRID 1757180 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-9cba33e6086249329a43f77e85476954
Source dataset
uspto-grants-1995_08
Patent number
US05444080

Reaction notes

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