Reaktion #6224

Reaktionsgleichung

4-hydroxypyridine

N-chloromethylphthalimide

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

→

desired compound

Ausbeute 21.0%

4-(phthalimidomethyloxy)pyridine

Ausbeute 21.0%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.DISTILLATIONAfter the solvent was distilled off
2. 2
   workup.ADDITIONthe reaction mixture was poured into water
3. 3
   Extraktionextracted with ethyl acetate
4. 4
   FiltrationThe precipitate was filtered off
5. 5
   ExtraktionThe aqueous layer was further extracted with ethyl acetate
6. 6
   WaschenThe organic layer was washed with water
7. 7
   Trocknendried over anhydrous magnesium sulfate
8. 8
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
9. 9
   SonstigeThe residue was purified by column chromatography (eluent: ethyl acetate)

Vorschrift

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).

Quelle