HCID 22055226, compound → HCID 178441829, compound

HRID 1917449Notes

Reaction equation

HRID 1917449 reaction equation
[C:1]([C:5]1[N:9]=[CH:8][NH:7][C:6]=1[CH2:10][OH:11])([CH3:4])([CH3:3])[CH3:2]>CC(C)=O.[O-2].[O-2].[Mn+4]>[C:1]([C:5]1[N:9]=[CH:8][NH:7][C:6]=1[CH:10]=[O:11])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 22055226HCID 22055226, compound

Product 1

HCID 178441829HCID 178441829, compoundYield 54.8%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 180AcetoneSolvent

Procedure

Manganese dioxide (30 g, 0.35 mol) was added to a heterogeneous solution of (5-tert-butyl-3H-imidazol-4-yl)-methanol (4.97 g, 0.03 mol) in acetone (700 ml) and the resulting mixture was stirred at room temperature for 4 h. The mixture was filtered through a pad of Celite and the pad was washed with acetone. The filtrate and washings were combined and evaporated. The residue was triturated with ether to afford, as a colorless solid, 5-tert-butyl-3H-imidazole-4-carbaldehyde (2.50 g, 51%). (Hayashi, Personal Communication (2000)).

Workup

  1. filtrationThe mixture was filtered through a pad of Celite
  2. washthe pad was washed with acetone
  3. customevaporated
  4. customThe residue was triturated with ether

Sources & evidence

ORD record
ord-b35d85690b284a73b8e2b59c21da17ed
Source dataset
uspto-grants-2013_12
Patent number
US08618292B2

Reaction notes

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