HCID 10607160, compound → HCID 178442313, compound

HRID 544971Notes

Reaction equation

HRID 544971 reaction equation
[CH3:1][C:2]([C:6]1[N:10]=[CH:9][NH:8][C:7]=1[CH2:11][OH:12])([CH3:5])[CH:3]=[CH2:4]>CC(C)=O.[O-2].[O-2].[Mn+4]>[CH3:5][C:2]([C:6]1[N:10]=[CH:9][NH:8][C:7]=1[CH:11]=[O:12])([CH3:1])[CH:3]=[CH2:4]

Participants

4

Reactant 1

HCID 10607160HCID 10607160, compound

Product 1

HCID 178442313HCID 178442313, compoundYield 55.4%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 180AcetoneSolvent

Procedure

Manganese dioxide (20 g, 0.23 mol) was added to a solution of [5-(1,1-dimethyl-allyl)-3H-imidazol-4-yl]-methanol (2.56 g, 0.02 mol) in acetone (300 ml) and the resulting mixture was stirred at room temperature for 5 h. The mixture was filtered through filter paper and the residue was washed with acetone. The filtrate and washings were combined and evaporated to afford 5-(1,1-dimethyl-allyl)-3H-imidazole-4-carbaldehyde (1.82 g, 51%). (Hayashi et al., J. Org. Chem., 65:8402-8405 (2000)).

Workup

  1. filtrationThe mixture was filtered
  2. filtrationthrough filter paper
  3. washthe residue was washed with acetone
  4. customevaporated

Sources & evidence

ORD record
ord-cb868639a6a94de28238ff3415dc0f27
Source dataset
uspto-grants-2011_05
Patent number
US07935704B2

Reaction notes

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