تفاعل #58578

معادلة التفاعل

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

المردود 44.0%

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

المردود 44.0%

المذيبات

DMSO

water

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةcooled to room temperature
2. 2
   استخلاصextracted with ethylacetate (3×150 mL)
3. 3
   غسيلThe combined organic extracts were washed with brine (200 mL)
4. 4
   تجفيفdried with MgSO4
5. 5
   أخرىevaporated in vacuo
6. 6
   أخرىto give the crude product that
7. 7
   أخرىwas purified by column chromatography (SiO2)

الإجراء التجريبي

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.

المصدر