Dimethylcarbamoyl Chloride → 4-(Tert-butyl-dimethyl-silanyloxymethyl)-6-methyl-pyridine-2-carbonitrile

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Reaction Steps

To a stirred solution of 4-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-pyridine 1-oxide (11.2 g, 44 mmol) in dichloromethane (100 ml) at room temperature, was added trimethylsilyl cyanide (7.1 ml, 53.2 mmol). After 15 min., dimethylcarbamyl chloride (4.8 ml, 53.2 mmol) was added and the stirring was continued for 24 hr. The mixture was then cooled in an ice bath and saturated aqueous sodium bicarbonate solution (100 ml) was added. After 1 hr., organic layer was separated, dried with anhydrous magnesium sulfate, filtered, and evaporated in vacuo. The residue was purified by silica gel column chromatography (eluent, ether:hexane (1:1)) to afford 8.8 g (76%) of 4-(tert-butyl-dimethyl-silanyloxymethyl)-6-methyl-pyridine-2-carbonitrile 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