2-Methylpyridine → 2-(Cyclohex-2-en-1-ylmethyl)-pyridine

Temperature

-78 °C

Following a modified version of the procedure given in J. M. Ontoria et al., Bioorg. Med. Chem. Lett. 16 (2006), 4026, a solution of 2-methyl-pyridine (0.50 g, 5.37 mmol) in 10 ml of anhydrous THF was cooled to −78° C. under an atmosphere of argon. n-Butyllithium (2.36 ml of a 2.5 M solution in hexane, 5.91 mmol) was added dropwise and the solution was stirred at −78° C. for 1 h. 3-bromo-cyclohexene (0.68 ml, 5.91 mmol) was added then dropwise and the temperature was allowed to rise to ambient temperature over 3 h. After stirring overnight, the mixture was quenched by addition of 20 ml of water and extracted twice with EA. The combined organic phases were washed with a saturated solution of sodium chloride, dried over sodium sulfate, filtered and evaporated to dryness to give 0.436 g of 2-(cyclohex-2-en-1-ylmethyl)-pyridine as an orange oil. This product was dissolved in 8.4 ml of ethanol, 5% palladium on charcoal (50% in water; 0.087 g) was added, and the mixture was hydrogenated under a hydrogen pressure of 3.2 bar for 4 h at room temperature. The catalyst was then filtered off and the filtrate was evaporated to dryness under reduced pressure to give 0.415 g of the title compound as an oil.

1. waitto rise to ambient temperature over 3 h
2. stirringAfter stirring overnight
3. customthe mixture was quenched by addition of 20 ml of water
4. extractionextracted twice with EA
5. washThe combined organic phases were washed with a saturated solution of sodium chloride
6. dry with materialdried over sodium sulfate
7. filtrationfiltered
8. customevaporated to dryness

ORD record

ord-62acb84bcaf745228d4e4ea891558a80

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08415336B2