Hydrochloric Acid → 1-(5-chloropyridin-2-yl)ethanol

Participants

Reaction Conditions

Reaction Steps

Copper iodide (148 mg), 1-ethoxyvinyltri-n-butyltin (2.97 mL), and bis(triphenylphosphine)palladium (II) chloride (183 mg) were added to a solution of 2-bromo-5-chloropyridine (1 g) in acetonitrile (30 mL), and the reaction solution was stirred in a nitrogen atmosphere at 100° C. for three hours. The reaction solution was returned to room temperature. 10 mL of 5 N hydrochloric acid was added, and the reaction solution was heated under reflux for 30 minutes. The reaction solution was returned to room temperature and neutralized with a 5 N sodium hydroxide solution. Diethyl ether was added to the reaction solution, and the organic layer was separated. The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was dissolved in tetrahydrofuran (30 mL) and methanol (10 mL). Sodium borohydride (492 mg) was added, and the reaction solution was stirred at room temperature for one hour. Water and diethyl ether were added to the reaction solution, and the organic layer was separated. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (elution solvent: hexane-diethyl ether) to obtain 503 mg of the title compound.

Provenance & Evidence