Hydrogen Peroxide → 4-tert-Butyl-2-methyl-pyridine 1-oxide

HRID 1446718Notes

Reaction equation

HRID 1446718 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:5]=[CH:4][N:3]=1.[OH:12]O>ClCCl.C[Re](=O)(=O)=O.[O-2].[O-2].[Mn+4]>[C:8]([C:6]1[CH:5]=[CH:4][N+:3]([O-:12])=[C:2]([CH3:1])[CH:7]=1)([CH3:11])([CH3:10])[CH3:9]

Participants

6

Reactant 2

HCID 784Hydrogen PeroxideHCID 132390254-(Tert-butyl)-2-methylpyridine

Product 1

HCID 594853984-tert-Butyl-2-methyl-pyridine 1-oxide

Reagents, catalysts & solvents 3

HCID 178418406HCID 178418406, compoundCatalystHCID 178477782HCID 178477782, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

Dissolve 2-methyl-4-tert-butyl-pyridine (16.60 g, 111.23 mmol) in dichloromethane (80 mL) and add methyltrioxorhenium (VII) (0.139 g, 0.56 mmol) with vigorous stirring. At ambient temperature, add 30% hydrogen peroxide (40 mL) and stir vigorously for 18 hours. Quench the reaction by adding drop wise aqueous manganese dioxide (100 mg in 20 mL). After the off-gassing ceases, the aqueous turns a cloudy gray, the layers are separated and the aqueous is re-extracted with dichloromethane (3×100 mL). The organics are pooled, desiccated, filtered and concentrated to yield the title compound analytically pure (16.60 g, 100.61 mmol). MS (ESI), m/z 166 (M+1).

Workup

  1. customQuench
  2. customthe reaction
  3. customAfter the off-gassing ceases, the aqueous turns a cloudy gray, the layers are separated
  4. extractionthe aqueous is re-extracted with dichloromethane (3×100 mL)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d7f77fef8d08430b908571ccad77fbd0
Source dataset
uspto-grants-2010_02
Patent number
US07666879B2

Reaction notes

Loading…