Реакция #168804

Уравнение реакции

Bromoacetaldehyde diethyl acetal

cesium carbonate

N,N-dimethylacetamide

5,6-dichloropyridin-3-ol

→

2,3-dichloro-5-(2,2-diethoxyethoxy)pyridine

Выход 88.4%

Растворители

ethyl acetate

Условия реакции

Обработка

1. 1
   Промывкаthe organic layer was washed with water
2. 2
   Сушкаdried over anhydrous sodium sulfate
3. 3
   Концентрированиеconcentrated under reduced pressure
4. 4
   ДругоеThe obtained residue was purified by silica gel column chromatography (Biotage, hexane:ethyl acetate=11:1 to 9:1)

Методика

Bromoacetaldehyde diethyl acetal (2.74 ml, 18.3 mmol) and cesium carbonate (9.93 g, 30.5 mmol) were added to an N,N-dimethylacetamide solution (10 ml) of 5,6-dichloropyridin-3-ol (1.0 g, 6.10 mmol), and stirred under a nitrogen atmosphere at 100° C. for 16 hours. Saline solution and ethyl acetate were added to the reaction solution, the organic layer was washed with 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=11:1 to 9:1) to obtain 2,3-dichloro-5-(2,2-diethoxyethoxy)pyridine (1.51 g, yield: 88%) as an orange oil.

Источник