Реакция #6235

Уравнение реакции

4-hydroxypyridine

N-(4bromobutyl)phthalimide

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

→

desired compound

Выход 17.8%

4-(4-phthalimidobutyloxy)pyridine

Выход 17.8%

Растворители

DMF

Условия реакции

Обработка

1. 1
   workup.DISTILLATIONAfter the solvent was distilled off
2. 2
   workup.ADDITIONthe mixture was poured into water
3. 3
   Экстракцияextracted with ethyl acetate
4. 4
   ПромывкаThe mixture was washed with water
5. 5
   Сушкаdried over anhydrous magnesium sulfate
6. 6
   workup.DISTILLATIONthe solvent was distilled off
7. 7
   ДругоеThe residue was purified by column chromatography (eluent: ethyl acetate)

Методика

To a solution of 4.76 g (50 mmol) of 4-hydroxypyridine and 15.52 g (55 mmol) of N-(4bromobutyl)phthalimide in 80 ml of DMF was added 8.23 ml (5 mmol) of 1,8-diazabicyclo[5.4.0]-7-undecene. The mixture was stirred at room temperature for 7 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 the solvent was distilled off. The residue was purified by column chromatography (eluent: ethyl acetate) to obtain 2.63 g of the desired compound (yield: 17.2%, colorless crystals).

Источник