Hydrochloric Acid → HCID 86641947, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-chloro-4-cyanopyridine (1.5 g) in dimethylformamide (10 ml), 1.52 g of phenol and 2.2 g of potassium carbonate were added, and the reaction solution was stirred overnight at 120° C. The reaction solution was cooled, then 1N hydrochloric acid was added, and the mixture was 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, and the residue obtained was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (98:2-50/50), chloroform/methanol (99.5:0.5-92:8)) to afford a crude product as a white solid. To a solution of the crude product in toluene (10 ml), 15 ml of diisobutylaluminum hydride (1.0M toluene solution) was added at −78° C., and the reaction solution was stirred at the same temperature for 2 hours. To the reaction solution were added water and a saturated aqueous ammonium chloride solution sequentially, and the mixture was 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, 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 yellow oil.

Provenance & Evidence