Reacción #6224

Ecuación de reacción

4-hydroxypyridine

N-chloromethylphthalimide

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

→

desired compound

Rendimiento 21.0%

4-(phthalimidomethyloxy)pyridine

Rendimiento 21.0%

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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).

Fuente