反应 #360696

反应方程式

1-(2-chloroethyl)pyrrolidine hydrochloride

3-bromothiophenol

Potassium carbonate

→

product

收率 32.0%

1-[2-(3-bromo-phenylsulfanyl)-ethyl]-pyrrolidine

收率 32.0%

溶剂

acetonitrile

反应条件

后处理

1. 1
   其他The reaction was kept in oil bath at 80° C.
2. 2
   温度to reflux for 18 h
3. 3
   过滤filtered
4. 4
   其他to remove excess inorganics
5. 5
   萃取the organics were extracted with saturated NaHCO3 and brine
6. 6
   干燥The organics were dried over Na2SO4
7. 7
   浓缩then concentrated under reduced pressure
8. 8
   其他The resulting crude oil was purified by flash chromatography
9. 9
   浓缩The fractions were concentrated

实验过程

1-(2-chloroethyl)pyrrolidine hydrochloride (1.0 equiv., 8.82 mmol) and 3-bromothiophenol (1.5 equiv., 13.23 mmol) were dissolved in acetonitrile (100 mL). Potassium carbonate (10.0 equiv., 88.2 mmol) was added to the reaction while stirring. The reaction was kept in oil bath at 80° C. to reflux for 18 h. The reaction was then cooled to room temperature and filtered to remove excess inorganics, and the organics were extracted with saturated NaHCO3 and brine. The organics were dried over Na2SO4 then concentrated under reduced pressure. The resulting crude oil was purified by flash chromatography using 4:6 EtOAc/hexanes. The fractions were concentrated to afford product as a yellow oil (792.3 mg, 32% yield). Rf=0.75 MS (ES+): m/z=287 LC retention time: 1.81 min.

来源