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

Temperature

100 °C

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.

1. customwas returned to room temperature
2. temperaturethe reaction solution was heated
3. temperatureunder reflux for 30 minutes
4. customwas returned to room temperature
5. customthe organic layer was separated
6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
7. customthe solvent was evaporated under reduced pressure
8. dissolutionThe residue was dissolved in tetrahydrofuran (30 mL)
9. additionSodium borohydride (492 mg) was added
10. stirringthe reaction solution was stirred at room temperature for one hour
11. additionWater and diethyl ether were added to the reaction solution
12. customthe organic layer was separated
13. washThe organic layer was washed with brine
14. dry with materialdried over anhydrous magnesium sulfate
15. customThe solvent was evaporated under reduced pressure
16. customthe residue was purified by silica gel column chromatography (elution solvent: hexane-diethyl ether)

ORD record

ord-008a2c42679d466187de320436dece78

Source dataset

uspto-grants-2009_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07618960B2