반응 #58578

반응 방정식

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

수율 44.0%

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

수율 44.0%

용매

DMSO

water

반응 조건

후처리

1. 1
   온도cooled to room temperature
2. 2
   추출extracted with ethylacetate (3×150 mL)
3. 3
   세척The combined organic extracts were washed with brine (200 mL)
4. 4
   건조dried with MgSO4
5. 5
   기타evaporated in vacuo
6. 6
   기타to give the crude product that
7. 7
   기타was purified by column chromatography (SiO2)

실험 절차

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.

출처