Реакция #48011

Уравнение реакции

2,3-bis(chloromethyl)pyridine hydrochloride

Sodium

diethyl malonate

→

5,7-dihydro-[1]pyrindine-6,6-dicarboxylic acid diethyl ester

Растворители

ethanol

ethanol

Условия реакции

Обработка

1. 1
   ТемператураThe reaction is heated
2. 2
   Температураto reflux for 5 hours
3. 3
   Фильтрацияfiltered
4. 4
   ДругоеThe filtrate is evaporated
5. 5
   Экстракцияextracted with ethyl acetate
6. 6
   ПромывкаThe combined organic phases are washed with brine
7. 7
   Сушкаdried (MgSO4)
8. 8
   Другоеevaporated
9. 9
   ДругоеThe crude product is purified by flash column chromatography (3:1-2:1 isohexanes-EtOAc gradient)

Методика

Sodium metal (0.345 g, 15.0 mmol) is dissolved in ethanol (20 ml) and diethyl malonate (0.713 g, 4.70 mmol) is added, followed by a suspension of 2,3-bis(chloromethyl)pyridine hydrochloride (Org. Process Res. Dev., 2002, 6, 938; 1.0 g, 4.70 mmol) in ethanol (15 ml) over 5 minutes. The reaction is heated to reflux for 5 hours, cooled to ambient temperature and filtered. The filtrate is evaporated, taken into water and extracted with ethyl acetate. The combined organic phases are washed with brine, dried (MgSO4) and evaporated. The crude product is purified by flash column chromatography (3:1-2:1 isohexanes-EtOAc gradient) to afford 5,7-dihydro-[1]pyrindine-6,6-dicarboxylic acid diethyl ester, MH+264.

Источник