Réaction #6224

Équation de réaction

4-hydroxypyridine

N-chloromethylphthalimide

1,8-diazabicyclo[5,4,0]-7-undecene

→

desired compound

Rendement 21.0%

4-(phthalimidomethyloxy)pyridine

Rendement 21.0%

Solvants

DMF

Conditions de réaction

Traitement

1. 1
   workup.DISTILLATIONAfter the solvent was distilled off
2. 2
   workup.ADDITIONthe reaction mixture was poured into water
3. 3
   Extractionextracted with ethyl acetate
4. 4
   FiltrationThe precipitate was filtered off
5. 5
   ExtractionThe aqueous layer was further extracted with ethyl acetate
6. 6
   LavageThe organic layer was washed with water
7. 7
   Séchagedried over anhydrous magnesium sulfate
8. 8
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
9. 9
   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 10.76 g (55 mmol) of N-chloromethylphthalimide 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 2 hours. After the solvent was distilled off, the reaction mixture was poured into water and extracted with ethyl acetate. The precipitate was filtered off. The aqueous layer was further extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by column chromatography (eluent: ethyl acetate) to obtain 2.67 g of the desired compound (yield: 21%, colorless crystals).

Source