Réaction #435006

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
   AutreThe resulting reaction mixture
2. 2
   Autrewas bubbled with nitrogen
3. 3
   workup.ADDITIONethyl acetate was added
4. 4
   FiltrationAfter the reaction mixture was filtered through celite
5. 5
   Autreto remove insoluble residue
6. 6
   Lavagethe filtrate was washed with water and brine
7. 7
   ExtractionThe obtained organic extract
8. 8
   Séchagewas dried over anhydrous magnesium sulfate
9. 9
   Filtrationfiltered
10. 10
    Autrethe solvent was evaporated under reduced pressure
11. 11
    Autrethe residue was purified by silica gel column chromatography

Mode opératoire

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.

Source