Reacción #435006

Ecuación de reacción

2-bromopyridine

1-butyne

→

title compound

Rendimiento 84.3%

2-(1-Butynyl)pyridine

Rendimiento 84.3%

Disolventes

diethylamine

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe resulting reaction mixture
2. 2
   Otrowas bubbled with nitrogen
3. 3
   workup.ADDITIONethyl acetate was added
4. 4
   FiltraciónAfter the reaction mixture was filtered through celite
5. 5
   Otroto remove insoluble residue
6. 6
   Lavadothe filtrate was washed with water and brine
7. 7
   ExtracciónThe obtained organic extract
8. 8
   Secadowas dried over anhydrous magnesium sulfate
9. 9
   Filtraciónfiltered
10. 10
    Otrothe solvent was evaporated under reduced pressure
11. 11
    Otrothe residue was purified by silica gel column chromatography

Procedimiento

To a solution of 2-bromopyridine (50 g) dissolved in diethylamine (500 mL) was added dichlorobis(triphenylphosphine)palladium(II) (2.2 g) and copper iodide (0.3 g), and the reaction mixture was stirred for 4 hours at room temperature while introducing 1-butyne (100 g) as a gas. The resulting reaction mixture was bubbled with nitrogen, and then ethyl acetate was added. After the reaction mixture was filtered through celite to remove insoluble residue, the filtrate was washed with water and brine. The obtained organic extract was dried over anhydrous magnesium sulfate and filtered, the solvent was evaporated under reduced pressure, the residue was purified by silica gel column chromatography and the title compound (35 g) was obtained as a brown oil from the n-hexane:ethyl acetate (5:1) fraction.

Fuente