[1-(4-fluorophenyl)-1H-imidazol-5-yl]methanol → 1-(4-fluorophenyl)-1H-imidazole-5-carbaldehyde

HRID 30623Notes

Reaction equation

HRID 30623 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH2:13][OH:14])=[CH:11][N:10]=[CH:9]2)=[CH:4][CH:3]=1>[O-2].[O-2].[Mn+4].O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12]([CH:13]=[O:14])=[CH:11][N:10]=[CH:9]2)=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 69209067[1-(4-fluorophenyl)-1H-imidazol-5-yl]methanol

Product 1

HCID 838773511-(4-fluorophenyl)-1H-imidazole-5-carbaldehydeYield 89%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of [1-(4-fluorophenyl)-1H-imidazol-5-yl]methanol (2.50 g), activated manganese dioxide (10 g) and tetrahydrofuran (150 ml) was stirred at room temperature for 3 hrs. The reaction mixture was filtered, and the organic layer was concentrated to give 1-(4-fluorophenyl)-1H-imidazole-5-carbaldehyde (2.20 g, 89%) as crystals. Recrystallization thereof from ethyl acetate-hexane gave pale-yellow prism crystals. melting point: 131-133° C.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe organic layer was concentrated

Sources & evidence

ORD record
ord-1134318c0a31425d84a12bb2bfaf4c53
Source dataset
uspto-grants-2008_09
Patent number
US07423159B2

Reaction notes

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