Hydrogen Peroxide → 4-(3-(tert-Butoxycarbonyl)phenyl)-3-methylpyridine 1-oxide

HRID 39453

Reaction equation

HRID 39453 reaction equation
[CH3:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[CH:9]=[C:10]([CH:18]=[CH:19][CH:20]=1)[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].[OH:21]O>ClCCl.C[Re](=O)(=O)=O>[C:14]([O:13][C:11]([C:10]1[CH:9]=[C:8]([C:7]2[CH:6]=[CH:5][N+:4]([O-:21])=[CH:3][C:2]=2[CH3:1])[CH:20]=[CH:19][CH:18]=1)=[O:12])([CH3:17])([CH3:15])[CH3:16]

Participants

5

Reactant 2

HCID 784Hydrogen PeroxideHCID 57895121Tert-butyl 3-(3-methylpyridin-4-yl)benzoate

Product 1

HCID 578951674-(3-(tert-Butoxycarbonyl)phenyl)-3-methylpyridine 1-oxide

Reagents, catalysts & solvents 2

HCID 178477782HCID 178477782, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 3-(3-methylpyridin-4-yl)benzoate (0.500 g, 1.86 mmol) was dissolved in a mixture of dichloromethane (0.800 mL) and 30% hydrogen peroxide (0.421 mL). Methyltrioxorhenium (VII) (2.3 mg, 0.92 mmol) was added and the reaction mixture was stirred vigorously for 5 hours. The layers were then separated and the organic layer was treated with sodium sulfite, and then dried over sodium sulfate. The crude product filtered, evaporated to dryness, and used without further purification. ESI-MS m/z calc. 285.1. found 286.1 (M+1)+. Retention time 1.22 minutes.

Workup

  1. customThe layers were then separated
  2. additionthe organic layer was treated with sodium sulfite
  3. dry with materialdried over sodium sulfate
  4. filtrationThe crude product filtered
  5. customevaporated to dryness
  6. customused without further purification

Sources & evidence

ORD record
ord-fd58781760844103bf1319174b525b1e
Source dataset
uspto-grants-2013_09
Patent number
US08524910B2

Linked notes

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