Hydrogen Peroxide → HCID 178481654, compound

HRID 658352Notes

Reaction equation

HRID 658352 reaction equation
[CH3:1][N:2]1[C:7]([S:8][CH3:9])=[CH:6][CH:5]=[C:4]([C:10]([C:12]2[C:13](=[O:19])[CH2:14][CH2:15][CH2:16][C:17]=2[OH:18])=[O:11])[C:3]1=[O:20].OO.[S:23]([O-:26])(O)=[O:24].[Na+].[CH3:28]O>[O-][W]([O-])(=O)=O.[Na+].[Na+]>[CH3:1][N:2]1[C:7]([S:8]([CH3:9])=[O:24])=[CH:6][CH:5]=[C:4]([C:10]([C:12]2[C:17](=[O:18])[CH2:16][CH2:15][CH2:14][C:13]=2[OH:19])=[O:11])[C:3]1=[O:20].[CH3:1][N:2]1[C:7]([S:23]([CH3:28])(=[O:26])=[O:24])=[CH:6][CH:5]=[C:4]([C:10]([C:12]2[C:17](=[O:18])[CH2:16][CH2:15][CH2:14][C:13]=2[OH:19])=[O:11])[C:3]1=[O:20]

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 887MethanolHCID 23665763Sodium BisulfiteHCID 178503198HCID 178503198, compound

Product 2

HCID 178481654HCID 178481654, compoundYield 29%HCID 178481655HCID 178481655, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 26052Sodium tungstateCatalyst

Procedure

2-[1,2-dihydro-1-methyl-6-methylthio-2-oxopyridine-3-carbonyl]-3-hydroxy-2-cyclohexen-1-one (1.2 g, 4.1 mmol), sodium tungstate (0.13 g, 0.4 mmol) and aqueous 35% hydrogen peroxide (0.48 g, 5.4 mmol) were dissolved in methanol (2 mL), and the mixture was stirred for 5 hours at room temperature. The mixed solution was poured into a sodium hydrogensulfite solution, and extracted with chloroform. The obtained organic layer was dried over anhydrous magnesium sulfate, the inorganic substance was separated by filtration, and then the solvent was distilled off under reduced pressure. Thus obtained residue was purified by column chromatography to obtain 0.36 g of 2-[1,2-dihydro-1-methyl-6-methylsulfinyl-2-oxopyridine-3-carbonyl]-3-hydroxy-2-cyclohexen-1-one (1.2 mmol, yield: 29%) and 0.16 g of 2-[1,2-dihydro-1-methyl-6-methylsulfonyl-2-oxopyridine-3-carbonyl]-3-hydroxy-2-cyclohexen-1-one (0.49 mmol, yield: 12%).

Workup

  1. extractionextracted with chloroform
  2. dry with materialThe obtained organic layer was dried over anhydrous magnesium sulfate
  3. customthe inorganic substance was separated by filtration
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThus obtained residue was purified by column chromatography

Sources & evidence

ORD record
ord-dca05356349d4bf2b981a4ef98f4a9ea
Source dataset
uspto-grants-2011_12
Patent number
US08076487B2

Reaction notes

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