Реакция #58578

Уравнение реакции

18-Crown-6

potassium cyanide

product

Toluene-4-sulfonic acid 1-benzyl-4-(4-bromo-thiophen-2-yl)-pyrrolidine-3-yl-methyl ester

→

subtitle compound

Выход 44.0%

[1-Benzyl-4-(4-bromo-thiophen-2-yl)-pyrrolidin-3-yl]-acetonitrile

Выход 44.0%

Растворители

DMSO

water

Условия реакции

Обработка

1. 1
   Температураcooled to room temperature
2. 2
   Экстракцияextracted with ethylacetate (3×150 mL)
3. 3
   ПромывкаThe combined organic extracts were washed with brine (200 mL)
4. 4
   Сушкаdried with MgSO4
5. 5
   Другоеevaporated in vacuo
6. 6
   Другоеto give the crude product that
7. 7
   Другоеwas purified by column chromatography (SiO2)

Методика

18-Crown-6 (5.3 g, 0.020 mol) and potassium cyanide (1.3 g, 0.020 mol) were added, respectively, to a solution of the product from step c) (6.7 g, 0.013 mol) in 50 mL of DMSO. The reaction mixture was heated at 80° C. overnight, cooled to room temperature, diluted with water (150 mL) and extracted with ethylacetate (3×150 mL). The combined organic extracts were washed with brine (200 mL), dried with MgSO4, and evaporated in vacuo to give the crude product that was purified by column chromatography (SiO2) using 1-100% ethylacetate-hexane gradient to give the subtitle compound (2.1 g, yield: 44%). MS calculated for C17H17BrN2S+H: 361, observed: 361 and 363.

Источник