Hydrogen Peroxide → 4-(2-{[tert-Butyl(dimethyl)silyl]oxy}ethyl)-1-oxo-1lambda~5~-pyridine

HRID 2420991Notes

Reaction equation

HRID 2420991 reaction equation
[O:1]([CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=1)[Si:2]([C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:4])[CH3:3].[OH:17]O.O>ClCCl.C[Re](=O)(=O)=O>[O:1]([CH2:9][CH2:10][C:11]1[CH:12]=[CH:13][N+:14]([O-:17])=[CH:15][CH:16]=1)[Si:2]([C:5]([CH3:7])([CH3:8])[CH3:6])([CH3:4])[CH3:3]

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 962WaterHCID 223216194-(Tert-butyldimethylsilyloxyethyl)-pyridine

Product 1

HCID 197577894-(2-{[tert-Butyl(dimethyl)silyl]oxy}ethyl)-1-oxo-1lambda~5~-pyridineYield 64%

Reagents, catalysts & solvents 2

HCID 178477782HCID 178477782, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

4-[2-(tert-Butyldimethylsiloxy)ethyl]pyridine (0.222 g, 1.00 mmol) obtained in Step 1 was dissolved in dichloromethane (2.00 mL), then methyltrioxorhenium (VII) (0.001 g, 0.005 mmol) and 30% aqueous hydrogen peroxide (1.00 mL) were added thereto, followed by stirring at room temperature for 2 hours. After completion of the reaction was confirmed by thin-layer chromatography, water was added to the reaction mixture, and the resulting mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure to give 4-[2-(tert-butyldimethylsiloxy)ethyl]pyridine-N-oxide (0.153 g, yield 64%).

Workup

  1. additionwas added to the reaction mixture
  2. extractionthe resulting mixture was extracted with dichloromethane
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-52850a419655478cb79c334fa2d565e0
Source dataset
uspto-grants-2011_06
Patent number
US07956060B2

Reaction notes

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