Реакция #84338

Уравнение реакции

water

1-(3,5-dichloropyridin-2-yl)ethanone

potassium carbonate

acetaldoxime

→

desired crude product

Выход 29.1%

1-(3-chloro-5-hydroxypyridin-2-yl)ethanone

Выход 29.1%

Растворители

dimethylsulfoxide

Условия реакции

Обработка

1. 1
   ДругоеAfter completion of the reaction
2. 2
   Температураto cool to room temperature
3. 3
   Промывкаwashed with diethyl ether (30 ml×1)
4. 4
   Экстракцияextracted with ethyl acetate (25 ml×2)
5. 5
   Сушкаdried over saturated aqueous sodium chloride
6. 6
   Другоеanhydrous sodium sulfate, and the solvent was evaporated under reduced pressure

Методика

To a solution of 3.8 g of the 1-(3,5-dichloropyridin-2-yl)ethanone prepared in Step 1 in Synthetic Example 2 and 13.8 g of potassium carbonate in 20 ml of dimethylsulfoxide, 5.9 g of acetaldoxime was added, and the mixture was stirred at 80° C. for 4 hours. After completion of the reaction, the reaction mixture was allowed to cool to room temperature, mixed with 50 ml of water and washed with diethyl ether (30 ml×1), the resulting aqueous layer was acidified with 6N aqueous hydrochloric acid and extracted with ethyl acetate (25 ml×2). The resulting organic layers were combined, dried over saturated aqueous sodium chloride and then anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain 1.0 g of desired crude product as brown crystals. The crystals were used in the next step without further purification.

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