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

HRID 345347Notes

Reaction equation

HRID 345347 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>C(Cl)Cl>[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-oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 40.6 g of 4-(tert-butyl-dimethylsilyloxymethyl)-pyridine and 40 g of m-chloroperbenzoic acid in 500 ml methylene chloride is stirred 16 hours at room temperature. Solution is washed with 2N sodium hydroxide and water, dried over sodium sulfate, filtered and concentrated in vacuo to yield 4-(tert-butyldimethylsilyloxymethyl)-pyridine-N-oxide.

Workup

  1. washSolution is washed with 2N sodium hydroxide and water
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-78453a56fcc94d8d89afdd9216dad558
Source dataset
uspto-grants-1991_10
Patent number
US05057506

Reaction notes

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