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

HRID 1164881Notes

Reaction equation

HRID 1164881 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 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, dried sodium sulfate
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-aa999dd686e746079be98fafedc04ddd
Source dataset
uspto-grants-1990_03
Patent number
US04906621

Reaction notes

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