Reacción #9274

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
   OtroAfter bubbling in nitrogen
2. 2
   Extracciónextraction
3. 3
   FiltraciónThe insoluble portion was filtered out with celite
4. 4
   Lavadothe organic layer was washed with water and brine
5. 5
   SecadoAfter drying over anhydrous magnesium sulfate and filtration
6. 6
   Concentraciónthe solvent was concentrated under reduced pressure
7. 7
   Otrothe residue was purified by silica gel column chromatography

Procedimiento

After dissolving 2-bromopyridine (50 g) in diethylamine (500 mL) and adding dichlorobis(triphenylphosphine)palladium (II) (2.2 g) and copper iodide (0.3 g), the mixture was stirred at room temperature for 4 hours while introducing 1-butyne (100 g) as a gas. After bubbling in nitrogen, extraction was performed with ethyl acetate. The insoluble portion was filtered out with celite, and then the organic layer was washed with water and brine. After drying over anhydrous magnesium sulfate and filtration, the solvent was concentrated under reduced pressure, the residue was purified by silica gel column chromatography, and the title compound (35 g) was obtained from the n-hexane:ethyl acetate (5:1) fraction as a brown oil.

Fuente