2-Bromopropane → (2-Isopropoxypyridin-3-yl)methanol

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 2-hydroxynicotinate (250 mg) in dimethylformamide (3 ml), 0.459 ml of 2-bromopropane and 676 mg of potassium carbonate were added, and the reaction solution was stirred at 50° C. for 5 hours and at 70° C. for 3 hours. The reaction solution was cooled, then a saturated aqueous ammonium chloride solution was added, and the mixture was extracted with ethyl acetate. The combined organic layers were washed with a saturated saline solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to afford a crude product as a colorless oil. To a solution of lithium aluminum hydride (247 mg) in tetrahydrofuran (2 ml), a solution of the crude product in tetrahydrofuran 3 ml was added under ice-cooling. The reaction solution was stirred for 2 hours under ice-cooling, followed by adding sodium sulfate decahydrate and further stirring the mixture 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 (98:2-50:50)) to afford the title compound as a colorless oil.

Provenance & Evidence