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

HRID 228826

Reaction equation

HRID 228826 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]([C:10]2[CH:15]=[C:14]([CH3:16])[CH:13]=[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]=[C:14]([CH3:16])[CH:13]=[CH:12][N:11]=2)=[O:9])[O:5][C:6]=1[CH3:7]

Participants

4

Reactant 1

HCID 23078475(4,5-Dimethylfuran-2-yl)-(4-methyl-pyridin-2-yl)-methanol

Product 1

HCID 23078347(4,5-Dimethylfuran-2-yl)-(4-methyl-pyridin-2-yl)-methanoneYield 77.4%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalyst2×HCID 6212ChloroformSolvent

Procedure

(4,5-Dimethylfuran-2-yl)-(4-methyl-pyridin-2-yl)-methanol (900 mg) was dissolved in chloroform (20 ml) to prepare a solution. Manganese dioxide (3.6 g) was added to the solution, and the mixture was stirred at room temperature overnight. Further, manganese dioxide (1.8 g) was then added to the reaction solution, and the mixture was stirred at room temperature for 5 hr. The reaction solution was filtered through Celite, and 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)-(4-methyl-pyridin-2-yl)-methanone (690 mg, yield 77%).

Workup

  1. customto prepare a solution
  2. stirringthe mixture was stirred at room temperature for 5 hr
  3. filtrationThe reaction solution was filtered through Celite
  4. customthe solvent was removed from the filtrate by distillation under the reduced pressure
  5. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-b79a5c0abf3748e197e2d1d621430bd9
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Linked notes

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