Pyridine → HCID 86754050, compound

Participants

Reaction Steps

To a solution of 4-cyano-4,4-diphenylbutan-1-ol (2.2 g, 8.7 mmol.) and pyridine (2.69 ml, 33 mmol.) in acetonitrile (20 ml) was added p-toluenesulfonyl chloride (1.66 g, 8.7 mmol.). To the mixture was added 4-dimethylaminopyridine (a catalytic amount), and the mixture was stirred for two hours at room temperature. To the reaction mixture was added ethyl acetate, which was washed with a 1N HCl and a saturated aqueous saline solution, and, then, dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The residue was dissolved in acetone (30 ml), to which was added sodium iodide (1.96 g, 13 mmol.). The mixture was refluxed for one hour. The solvent was distilled off under reduced pressure. To the residue was added water, which was subjected to extraction with ethyl acetate. The organic layer was washed with a saturated aqueous saline solution and a dilute aqueous solution of sodium thiosulfate, followed by drying over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The residue was subjected to a silica gel column chromatography, eluting with ethyl acetate, to afford the title compound (1.3 g).

Provenance & Evidence