(4,5-Dimethylfuran-2-yl)-(5-methyl-pyridin-2-yl)methanol → (4,5-Dimethylfuran-2-yl)-(5-methyl-pyridin-2-yl)-methanone

HRID 228822Notes

Reaction equation

HRID 228822 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][N:11]=2)[OH:9])[O:5][C:6]=1[CH3:7]>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH3:1][C:2]1[CH:3]=[C:4]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][N:11]=2)=[O:9])[O:5][C:6]=1[CH3:7]

Participants

4

Reactant 1

HCID 23078454(4,5-Dimethylfuran-2-yl)-(5-methyl-pyridin-2-yl)methanol

Product 1

HCID 23078334(4,5-Dimethylfuran-2-yl)-(5-methyl-pyridin-2-yl)-methanoneYield 93.6%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

(4,5-Dimethylfuran-2-yl)-(5-methyl-pyridin-2-yl)methanol (850 mg) was dissolved in chloroform (40 ml) to prepare a solution. Manganese dioxide (3.4 g) was added to the solution, and the mixture was stirred at room temperature overnight. The reaction solution was filtered through Celite. The solvent was removed from the filtrate by distillation under the reduced pressure, and the residue was purified by column chromatography using hexane-ethyl acetate to give (4,5-dimethylfuran-2-yl)-(5-methyl-pyridin-2-yl)-methanone (788 mg, yield 93%).

Workup

  1. customto prepare a solution
  2. filtrationThe reaction solution was filtered through Celite
  3. customThe solvent was removed from the filtrate by distillation under the reduced pressure
  4. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-42f780a8918d4da58487b79b159fe1d8
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

Loading…