Реакция #9274

Уравнение реакции

2-bromopyridine

1-butyne

→

title compound

Выход 84.3%

2-(1-Butynyl)pyridine

Выход 84.3%

Растворители

diethylamine

Условия реакции

Обработка

1. 1
   ДругоеAfter bubbling in nitrogen
2. 2
   Экстракцияextraction
3. 3
   ФильтрацияThe insoluble portion was filtered out with celite
4. 4
   Промывкаthe organic layer was washed with water and brine
5. 5
   СушкаAfter drying over anhydrous magnesium sulfate and filtration
6. 6
   Концентрированиеthe solvent was concentrated under reduced pressure
7. 7
   Другоеthe residue was purified by silica gel column chromatography

Методика

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.

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