Isopropyl iodide → [2-(Propan-2-ylsulfanyl)pyridin-3-yl]methanol

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-mercaptonicotinic acid (700 mg) in dimethylformamide (7 ml), 1.35 ml of 2-iodopropane and 541 mg of sodium hydride were added under ice-cooling, and the reaction solution was stirred at room temperature for 4 hours, at 60° C. for 2 hours. The reaction solution was cooled, then diluted with a saturated aqueous ammonium chloride solution, and extracted with ethyl acetate. The combined organic layers were washed with a saturated saline solution and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to afford a crude product as a yellow oil. To a solution of lithium aluminum hydride (428 mg) in tetrahydrofuran (7 ml), a solution of the crude product in tetrahydrofuran (3 ml) was added under ice-cooling, and the reaction solution was stirred at the same temperature for 30 minutes. To the reaction solution was added sodium sulfate decahydrate, and the mixture was further stirred at the same temperature for 1 hour. The reaction solution was Celite-filtered, the filtrate was distilled off under reduced pressure, and the residue obtained was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (95:5-50:50)) to afford the title compound as a colorless oil.

Provenance & Evidence