m-Chloroperbenzoic acid → 4-(Tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-pyridine 1-oxide

HRID 426245Notes

Reaction equation

HRID 426245 reaction equation
[C:1]([SiH2:5][O:6][C:7]([CH3:16])([CH3:15])[C:8]1[CH:13]=[CH:12][N:11]=[C:10]([CH3:14])[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].C1C=C(Cl)C=C(C(OO)=[O:25])C=1>ClCCl>[C:1]([SiH2:5][O:6][C:7]([CH3:16])([CH3:15])[C:8]1[CH:13]=[CH:12][N+:11]([O-:25])=[C:10]([CH3:14])[CH:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 1317294284-(tert-Butyl-dimethyl-silanyloxymethyl)-2-methyl-pyridine

Product 1

HCID 1317294304-(Tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-pyridine 1-oxideYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(tert-Butyl-dimethyl-silanyloxymethyl)-2-methyl-pyridine (11.47 g, 0.248.4 mmol) was stirred with 57-80% m-CPBA (25.8 g) in dichloromethane (100 ml) in a water bath for 24 hr. The mixture was evaporated in vacuo and the residue was purified by silica gel column chromatography (eluent, ether:hexane (3:1)) to afford 11.3 g (93%) of 4-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-pyridine 1-oxide as a white solid. 1H NMR (200 MHz, CDCl3) δ 0.11 (6H, s), 0.94 (9H, s), (3H, s), 2.52 (3H, s), 4.67 (2H, s), 6.97 (1H, d, J=6.7 Hz), 7.08 (1H, s), 8.10 (1H, d, J=6.7 Hz).

Workup

  1. customThe mixture was evaporated in vacuo
  2. customthe residue was purified by silica gel column chromatography (eluent, ether:hexane (3:1))

Sources & evidence

ORD record
ord-d03680b3396547f6b291282418a47c49
Source dataset
uspto-grants-2012_01
Patent number
US08106064B2

Reaction notes

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