Réaction #792209

Équation de réaction

potassium tert-butoxide

3-acetopyridine

ethyl 6-bromo-2-pyridinecarboxylate

water

→

1-(6-Bromopyridin-2-yl)-3-(pyridin-3-yl)propane-1,3-dione

Solvants

tetrahydrofuran

acetic acid

Conditions de réaction

Traitement

1. 1
   Autrehas formed
2. 2
   Extractionthe aqueous phase was subsequently extracted with dichloromethane
3. 3
   SéchageThe combined organic phases were dried over magnesium sulfate
4. 4
   Autrethe solvent was then removed under reduced pressure
5. 5
   AutreThe residue that remained was purified chromatographically (mobile phase: cyclohexane/ethyl acetate)
6. 6
   Lavagethe solid was then washed with diethyl ether

Mode opératoire

3.71 g (33.0 mmol) of potassium tert-butoxide were added to a mixture of 4.00 g (33.0 mmol) of 3-acetopyridine and 7.60 g (33.0 mmol) of ethyl 6-bromo-2-pyridinecarboxylate in 100 ml of tetrahydrofuran. The solution was stirred at room temperature until a solid mixture has formed. 100 ml of water and 10 ml of acetic acid were then added, and the aqueous phase was subsequently extracted with dichloromethane. The combined organic phases were dried over magnesium sulfate, and the solvent was then removed under reduced pressure. The residue that remained was purified chromatographically (mobile phase: cyclohexane/ethyl acetate), the solid was then washed with diethyl ether. This gave 6.91 g (69% of theory) of 1-(6-bromopyridin-2-yl)-3-(pyridin-3-yl)propane-1,3-dione.

Source