Hydrogen Peroxide → 4-[2-(4-Fluoro-phenyl)-1,1-dimethoxy-ethyl]-pyridine 1-oxide

HRID 659949

Reaction equation

HRID 659949 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)([O:12][CH3:13])[O:10][CH3:11])=[CH:4][CH:3]=1.[OH:20]O>ClCCl.C[Re](=O)(=O)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([C:14]2[CH:15]=[CH:16][N+:17]([O-:20])=[CH:18][CH:19]=2)([O:10][CH3:11])[O:12][CH3:13])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 784Hydrogen PeroxideHCID 149562264-[2-(4-Fluoro-phenyl)-1,1-dimethoxy-ethyl]-pyridine

Product 1

HCID 684293414-[2-(4-Fluoro-phenyl)-1,1-dimethoxy-ethyl]-pyridine 1-oxide

Reagents, catalysts & solvents 2

HCID 178477782HCID 178477782, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

55 g (0.21 mole) of 4-[2-(4-Fluoro-phenyl)-1,1-dimethoxy-ethyl]-pyridine and 445 mg of methyltrioxorhenium are dissolved in 250 mL of dichloromethane. 112 mL of commercial hydrogen peroxide solution is added to the reaction mixture which is further stirred over night at room temperature. The reaction mixture is then decanted and the organic phase is washed with sodium hydrogen sulfate and water and dried over magnesium sulfate. After concentration, 33 g of 4-[2-(4-Fluoro-phenyl)-1,1-dimethoxy-ethyl]-pyridine 1-oxide is obtained as a green oil.

Workup

  1. customThe reaction mixture is then decanted
  2. washthe organic phase is washed with sodium hydrogen sulfate and water
  3. dry with materialdried over magnesium sulfate
  4. concentrationAfter concentration

Sources & evidence

ORD record
ord-fae9c6c33f6a453e8bf832c89648a41c
Source dataset
uspto-grants-2011_12
Patent number
US08084395B2

Linked notes

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