Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate) → 4-[2-[2-[(2-chloro)-ethoxy]-phenyl]-ethenyl]-1H-indole

HRID 1906192Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1906192
[NH:1]1[C:9]2[C:4](=[C:5]([CH:10]=[CH:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[OH:18])[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.S(O[CH2:30][CH2:31][Cl:32])(C1C=CC(C)=CC=1)(=O)=O>[OH-].[Na+].O>[Cl:32][CH2:31][CH2:30][O:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[CH:11]=[CH:10][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:4]=1[CH:3]=[CH:2][NH:1]2

Komponenten

5

Edukt 2

HCID 6639Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate)HCID 541413862-[(1H-indol-4-yl)-ethenyl]-phenol

Produkt 1

HCID 542356984-[2-[2-[(2-chloro)-ethoxy]-phenyl]-ethenyl]-1H-indoleAusbeute 39,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

4 g of 2-[(1H-indol-4-yl)-ethenyl]-phenol obtained in Step A of Example 1 in 100 ml of 2N sodium hydroxide after having added 6 g of 2-chloroethanol tosylate were heated for 6 hours at reflux and the mixture was left for 16 hours at ambient temperature, then diluted with water and extracted with ethyl acetate. After eliminating the solvent under reduced pressure and chromatography on silica (eluent: benzene), 2 g of 4-[2-[2-[(2-chloro)-ethoxy]-phenyl]-ethenyl]-1H-indole (trans E) were obtained.

Aufarbeitung

  1. temperaturewere heated for 6 hours
  2. temperatureat reflux
  3. extractionextracted with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-f69f9a797ebb4410b183cea7efe2b7f4
Quelldatensatz
uspto-grants-1987_03
Patentnummer
US04650811

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