Reaction #792209

Reaction equation

potassium tert-butoxide

3-acetopyridine

ethyl 6-bromo-2-pyridinecarboxylate

water

→

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

Solvents

tetrahydrofuran

acetic acid

Conditions

Workup

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

Procedure

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