2-Methylpyridine → HCID 22610115, compound

Temperature

-78 °C

2-Picoline (5 g, 54 mmol) is dissolved in THF (100 mL) and cooled to −78° C. N-Butyllithium (40 mL of a 1.6M solution in THF, 64.3 mmol) was added to the solution over 10 minutes. The reaction mixture was then warmed to room temperature for 5 minutes and then cooled back down to −78° C. Then cyclohexylmethyl bromide (10 g, 57 mmol) was added, the reaction was warmed to room temperature and allowed to stir overnight. The reaction was then heated at reflux for 6 hours and then cooled to room temperature. The solvent was removed under vacuum and water and ethyl acetate were then added to the residue. The layers were separated and the aqueous was extracted with ethyl acetate. The organic extracts were combined, dried over anhydrous magnesium sulfate, filtered and concentrated to provide a dark oil. The oil was purified by flash chromatography to provide 2-pyridyl-1-cyclohexylethane (9 g, 89%).

1. temperatureThe reaction mixture was then warmed to room temperature for 5 minutes
2. temperaturecooled back down to −78° C
3. temperaturethe reaction was warmed to room temperature
4. temperatureThe reaction was then heated
5. temperatureat reflux for 6 hours
6. temperaturecooled to room temperature
7. customThe solvent was removed under vacuum and water and ethyl acetate
8. additionwere then added to the residue
9. customThe layers were separated
10. extractionthe aqueous was extracted with ethyl acetate
11. dry with materialdried over anhydrous magnesium sulfate
12. filtrationfiltered
13. concentrationconcentrated
14. customto provide a dark oil
15. customThe oil was purified by flash chromatography

ORD record

ord-f5661652018b46ea811aebc2e4eabefa

Source dataset

uspto-grants-2002_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06465453B1