Réaction #9274

Équation de réaction

2-bromopyridine

1-butyne

→

title compound

Rendement 84.3%

2-(1-Butynyl)pyridine

Rendement 84.3%

Solvants

diethylamine

Conditions de réaction

Traitement

1. 1
   AutreAfter bubbling in nitrogen
2. 2
   Extractionextraction
3. 3
   FiltrationThe insoluble portion was filtered out with celite
4. 4
   Lavagethe organic layer was washed with water and brine
5. 5
   SéchageAfter drying over anhydrous magnesium sulfate and filtration
6. 6
   Concentrationthe solvent was concentrated under reduced pressure
7. 7
   Autrethe residue was purified by silica gel column chromatography

Mode opératoire

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.

Source