Réaction #58578

Équation de réaction

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

Rendement 44.0%

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

Rendement 44.0%

Solvants

DMSO

water

Conditions de réaction

Traitement

1. 1
   Températurecooled to room temperature
2. 2
   Extractionextracted with ethylacetate (3×150 mL)
3. 3
   LavageThe combined organic extracts were washed with brine (200 mL)
4. 4
   Séchagedried with MgSO4
5. 5
   Autreevaporated in vacuo
6. 6
   Autreto give the crude product that
7. 7
   Autrewas purified by column chromatography (SiO2)

Mode opératoire

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.

Source