Реакция #168808

Уравнение реакции

Bromoacetaldehyde diethyl acetal

cesium carbonate

N,N-dimethylacetamide

6-fluoropyridin-3-ol

→

5-(2,2-diethoxyethoxy)-2-fluoropyridine

Выход 99.3%

Растворители

water

Условия реакции

Обработка

1. 1
   workup.ADDITIONwas added
2. 2
   Экстракцияextracted with ethyl acetate
3. 3
   ПромывкаThe organic layer was washed with water and saturated saline water
4. 4
   Сушкаdried over anhydrous sodium sulfate
5. 5
   Концентрированиеconcentrated under reduced pressure
6. 6
   ДругоеThe obtained residue was purified by silica gel column chromatography (Biotage, hexane:ethyl acetate=17:1 to 6:1)

Методика

Bromoacetaldehyde diethyl acetal (6.75 ml, 44.9 mmol) and cesium carbonate (30.9 g, 95.0 mmol) were added to an N,N-dimethylacetamide solution (60 ml) of 6-fluoropyridin-3-ol (3.0 g, 24.9 mmol, purity: at most 94%), and stirred under a nitrogen atmosphere at 100° C. for 15 hours. The reaction solution was cooled with ice, water was added, and extracted with ethyl acetate. The organic layer was washed with water and saturated saline water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (Biotage, hexane:ethyl acetate=17:1 to 6:1) to obtain 5-(2,2-diethoxyethoxy)-2-fluoropyridine (5.67 g, yield: 99%) as a pale yellow oil.

Источник