Reaktion #360696

Reaktionsgleichung

1-(2-chloroethyl)pyrrolidine hydrochloride

3-bromothiophenol

Potassium carbonate

→

product

Ausbeute 32.0%

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

Ausbeute 32.0%

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction was kept in oil bath at 80° C.
2. 2
   Temperaturto reflux for 18 h
3. 3
   Filtrationfiltered
4. 4
   Sonstigeto remove excess inorganics
5. 5
   Extraktionthe organics were extracted with saturated NaHCO3 and brine
6. 6
   TrocknenThe organics were dried over Na2SO4
7. 7
   Einengenthen concentrated under reduced pressure
8. 8
   SonstigeThe resulting crude oil was purified by flash chromatography
9. 9
   EinengenThe fractions were concentrated

Vorschrift

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.

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