Réaction #6244

Équation de réaction

4-hydroxypyridine

N-(2-bromoethyl)phthalimide

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

→

desired compound

Rendement 3.1%

4-(2-phthalimidoethyloxy)pyridine

Rendement 3.1%

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 13.97 g (55 mmol) of N-(2-bromoethyl)phthalimide in 80 ml of DMF, 8.23 ml (55 mmol) of 1,8-diazabicyclo[5.4.0]-7-undecene was added. The mixture was stirred at room temperature for 32 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 then the solvent was distilled off. The residue was purified by column chromatography (eluent: ethyl acetate) to obtain 0.41 g of the desired compound (yield: 3.1%, colorless crystal).

Source