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

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Reaction Steps

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).

Provenance & Evidence