Reaktion #9274

Reaktionsgleichung

2-bromopyridine

1-butyne

→

title compound

Ausbeute 84.3%

2-(1-Butynyl)pyridine

Ausbeute 84.3%

Lösungsmittel

diethylamine

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeAfter bubbling in nitrogen
2. 2
   Extraktionextraction
3. 3
   FiltrationThe insoluble portion was filtered out with celite
4. 4
   Waschenthe organic layer was washed with water and brine
5. 5
   TrocknenAfter drying over anhydrous magnesium sulfate and filtration
6. 6
   Einengenthe solvent was concentrated under reduced pressure
7. 7
   Sonstigethe residue was purified by silica gel column chromatography

Vorschrift

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.

Quelle