Reaktion #435006

Reaktionsgleichung

2-bromopyridine

1-butyne

→

title compound

Ausbeute 84.3%

2-(1-Butynyl)pyridine

Ausbeute 84.3%

Lösungsmittel

diethylamine

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe resulting reaction mixture
2. 2
   Sonstigewas bubbled with nitrogen
3. 3
   workup.ADDITIONethyl acetate was added
4. 4
   FiltrationAfter the reaction mixture was filtered through celite
5. 5
   Sonstigeto remove insoluble residue
6. 6
   Waschenthe filtrate was washed with water and brine
7. 7
   ExtraktionThe obtained organic extract
8. 8
   Trocknenwas dried over anhydrous magnesium sulfate
9. 9
   Filtrationfiltered
10. 10
    Sonstigethe solvent was evaporated under reduced pressure
11. 11
    Sonstigethe residue was purified by silica gel column chromatography

Vorschrift

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.

Quelle