反应 #58578

反应方程式

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

收率 44.0%

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

收率 44.0%

溶剂

DMSO

water

反应条件

后处理

1. 1
   温度cooled to room temperature
2. 2
   萃取extracted with ethylacetate (3×150 mL)
3. 3
   洗涤The combined organic extracts were washed with brine (200 mL)
4. 4
   干燥dried with MgSO4
5. 5
   其他evaporated in vacuo
6. 6
   其他to give the crude product that
7. 7
   其他was purified by column chromatography (SiO2)

实验过程

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.

来源