Réaction #6235

Équation de réaction

4-hydroxypyridine

N-(4bromobutyl)phthalimide

1,8-diazabicyclo[5.4.0]-7-undecene

→

desired compound

Rendement 17.8%

4-(4-phthalimidobutyloxy)pyridine

Rendement 17.8%

Solvants

DMF

Conditions de réaction

Traitement

1. 1
   workup.DISTILLATIONAfter the solvent was distilled off
2. 2
   workup.ADDITIONthe mixture was poured into water
3. 3
   Extractionextracted with ethyl acetate
4. 4
   LavageThe mixture was washed with water
5. 5
   Séchagedried over anhydrous magnesium sulfate
6. 6
   workup.DISTILLATIONthe solvent was distilled off
7. 7
   AutreThe residue was purified by column chromatography (eluent: ethyl acetate)

Mode opératoire

To a solution of 4.76 g (50 mmol) of 4-hydroxypyridine and 15.52 g (55 mmol) of N-(4bromobutyl)phthalimide in 80 ml of DMF was added 8.23 ml (5 mmol) of 1,8-diazabicyclo[5.4.0]-7-undecene. The mixture was stirred at room temperature for 7 hours. After the solvent was distilled off, the mixture was poured into water and extracted with ethyl acetate. The mixture was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off. The residue was purified by column chromatography (eluent: ethyl acetate) to obtain 2.63 g of the desired compound (yield: 17.2%, colorless crystals).

Source