m-Chloroperbenzoic acid → 4-(tert-Butyldimethylsilanyloxymethyl)pyridine 1-oxide

HRID 2202588Notes

Reaction equation

HRID 2202588 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].ClC1C=CC=C(C(OO)=[O:24])C=1>ClCCl>[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[CH:12][N+:13]([O-:24])=[CH:14][CH:15]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 109878804-(Tert-butyldimethylsilyloxymethyl)pyridine

Product 1

HCID 217815154-(tert-Butyldimethylsilanyloxymethyl)pyridine 1-oxideYield 100.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under a nitrogen atmosphere, 4-(tert-butyldimethylsilyloxymethyl)pyridine (1.1 g, 5 mmol) synthesized in Production Example 84 was dissolved in dichloromethane, and m-chloroperbenzoic acid (1.9 g, 14.5 mmol) was added slowly thereto under an ice cooling. The mixture was heated slowly to a room temperature and then stirred overnight. After the completion of the reaction was confirmed by HPLC, an excess of m-chloroperbenzoic acid was removed by a sodium thiosulfate solution. The remaining mixture was washed with 2-N sodium hydroxide 3 times. The organic layer was dried over magnesium sulfate, and the solvent was distilled off. Thus the title compound (1.2 g, 100%) was obtained as an oily substance.

Workup

  1. customan excess of m-chloroperbenzoic acid was removed by a sodium thiosulfate solution
  2. washThe remaining mixture was washed with 2-N sodium hydroxide 3 times
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-5f8511336aa94089a41e9388be19a138
Source dataset
uspto-grants-2016_06
Patent number
US09365553B2

Reaction notes

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