Réaction #9282

Équation de réaction

2-bromo-3-methoxypyridine

1-butyne

diethylamine

→

2-(1-butynyl)-4-methoxypyridine

Conditions de réaction

Traitement

1. 1
   Autrewas bubbled through at room temperature
2. 2
   AutreUpon completion of the reaction
3. 3
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
4. 4
   workup.ADDITIONWater was added to the obtained residue, extraction
5. 5
   Lavagethe extract was washed with brine
6. 6
   Séchagedried over magnesium sulfate
7. 7
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure

Mode opératoire

After adding dichlorobis(triphenylphosphine)palladium (II) (671 mg) and copper iodide (91 mg) to a solution of 2-bromo-3-methoxypyridine (18.0 g) in diethylamine (250 mL), 1-butyne (15.5 g) was bubbled through at room temperature, and the mixture was stirred for 20 hours. Upon completion of the reaction, the solvent was distilled off under reduced pressure. Water was added to the obtained residue, extraction was performed with ethyl acetate, the extract was washed with brine and dried over magnesium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was subjected to silica gel column chromatography (500 g), and 2-(1-butynyl)-4-methoxypyridine (10.0 g) was obtained from the n-hexane:ethyl acetate (2:1) fraction as a brown oil.

Source