Реакция #6224

Уравнение реакции

4-hydroxypyridine

N-chloromethylphthalimide

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

→

desired compound

Выход 21.0%

4-(phthalimidomethyloxy)pyridine

Выход 21.0%

Растворители

DMF

Условия реакции

Обработка

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

Методика

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).

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