Réaction #50762

Équation de réaction

3-bromopyridine

3-butyn-1-ol

triethylamine

water

→

4-(3-pyridyl)-1-but-3-ynol

Rendement 12.3%

Solvants

DCM

ethyl acetate

Conditions de réaction

Traitement

1. 1
   TempératureThe mixture was refluxed for 20 h under argon
2. 2
   TempératureAfter cooling
3. 3
   Extractionthe product extracted into DCM
4. 4
   SéchageThe combined organics were dried over anhydrous potassium carbonate
5. 5
   Filtrationfiltered
6. 6
   Autreevaporated
7. 7
   Autreto give a brown oil

Mode opératoire

To a stirred solution of 3-bromopyridine (3.75 g, 23.8 mmol), 3-butyn-1-ol (2.0 g, 28.5 mmol) and triethylamine (12 ml) in anhydrous DCM was added bis(triphenylphosphine)palladium dichloride (0.05 g, 0.07 mmol) and copper(I) iodide (0.05 g, 0.26 mmol). The mixture was refluxed for 20 h under argon. After cooling, water (20 ml) was added and the product extracted into DCM. The combined organics were dried over anhydrous potassium carbonate, filtered and evaporated to give a brown oil. Column chromatography (flash silica gel, ethyl acetate) gave 4-(3-pyridyl)-1-but-3-ynol (0.43 g, 12%) as a colourless oil.

Source