Hexane → 2-Methyl-5-vinylpyridine

To a suspension of methyltriphenylphosphonium bromide (62.54 g, 0.175 mol) in THF (150 mL) at −78° C. under nitrogen was added 2.5 M of n-butyllithium in hexane (69 mL, 0.17 mol) over a period of 1 hr. The mixture was warmed to room temperature to give a deep yellow ylide solution. To the ylide solution, cooled in ice, was introduced a solution of 6-methylnicotinaldehyde (18.63 g, 0.146 mol) in THF (50 mL). The reaction mixture was warmed to room temperature and stirred for 2 hours. The resulting suspension was heated to 60° C. over 30 minutes and stirred at 60° C. for 1 hour. After cooling, the reaction mixture was diluted with water and extracted with EtOAc. The organic layer was separated and washed with brine, dried (MgSO4), and concentrated. The residue was purified by silica gel column (0-10% EtOAc/hexane) to afford the title compound.

1. customto give a deep yellow ylide solution
2. temperatureTo the ylide solution, cooled in ice
3. temperatureThe reaction mixture was warmed to room temperature
4. temperatureThe resulting suspension was heated to 60° C. over 30 minutes
5. stirringstirred at 60° C. for 1 hour
6. temperatureAfter cooling
7. extractionextracted with EtOAc
8. customThe organic layer was separated
9. washwashed with brine
10. dry with materialdried (MgSO4)
11. concentrationconcentrated
12. customThe residue was purified by silica gel column (0-10% EtOAc/hexane)

ORD record

ord-fb3173a433044c97898e4faad1682a71

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08946439B2