Ethanol → 4-tert-Butylpyridine-2-carbonitrile

Participants

Reaction Conditions

Reaction Steps

To stirred dimethyl sulfate (6.70 g) was added slowly 4-tert-butyl-1-oxypyridine (8.0 g) at ca. 10° C. in an ice-water bath and the mixture was stirred for 3 hours at 80° C. After cooling to room temperature, to the mixture was added a mixture of ethanol and water (1:1, 60 ml) under stirring. To the mixture was added dropwise an aqueous solution of potassium cyanate (6.9 g in 20 ml of water) below 10° C. and stirring for 1 hour under the same condition, and then overnight at room temperature. To the resultant mixture was added 150 ml of water and the resultant mixture was extracted with CHCl3. The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. A crude compound was purified by column chromatography on silica gel with a mixture of ethyl acetate and n-hexane to give 4-tert-butyl-2-cyanopyridine (4.6 g) as a yellow oil.

Provenance & Evidence