Reaktion #685005

ord-a4567b16afe646408f7190ec9fefe142

Reaktionsgleichung

OCCCOCCc1cccc2sccc12
3-(2-(1-benzothiophene-4-yl)ethoxy)-1-propanol
O=S(Cl)Cl
thionyl chloride
CN(C)C=O
N,N-dimethylformamide
ClCCCOCCc1cccc2sccc12
yellow oil
ClCCCOCCc1cccc2sccc12
4-(2-(3-chloropropoxy)ethyl)-1-benzothiophene

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Temperaturthe obtained mixture was then heated
  2. 2
    Temperaturto reflux for 5 hours
  3. 3
    workup.DISTILLATIONSubsequently, the solvent was distilled away under a reduced pressure
  4. 4
    SonstigeThe residue was purified by column chromatography (eluent; hexane:ethyl acetate=20:1)

Vorschrift

1.40 g of 3-(2-(1-benzothiophene-4-yl)ethoxy)-1-propanol was dissolved in 7.0 ml of methylene chloride. Thereafter, 1.10 ml of thionyl chloride and 0.05 ml of N,N-dimethylformamide were added to the obtained solution, and the obtained mixture was then heated to reflux for 5 hours. Subsequently, the solvent was distilled away under a reduced pressure. The residue was purified by column chromatography (eluent; hexane:ethyl acetate=20:1), so as to obtain 1.43 g of a yellow oil product, 4-(2-(3-chloropropoxy)ethyl)-1-benzothiophene.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07897594B2uspto-grants-2011_03