反応 #58578

反応方程式

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

収率 44.0%

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

収率 44.0%

溶媒

DMSO

water

反応条件

後処理

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

実験手順

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.

出典