Water → 7-(3-chloropropoxy)-1H-indole

HRID 266978

Reaktionsgleichung

Reaktionsgleichung von HRID 266978
[H-].[Na+].[OH:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][CH:10]=[CH:9]2.Br[CH2:14][CH2:15][CH2:16][Cl:17].O>CN(C)C=O>[Cl:17][CH2:16][CH2:15][CH2:14][O:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][CH:10]=[CH:9]2

Komponenten

6

Edukt 4

HCID 962WaterHCID 80061-Bromo-3-chloropropaneHCID 24758Sodium hydrideHCID 27376517-Hydroxyindole

Produkt 1

HCID 153849647-(3-chloropropoxy)-1H-indole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel3×

Versuchsvorschrift

To a stirred suspension of sodium hydride (0.8 g, 17 mmol of a 50% oil dispersion) in dimethylformamide (20 ml), under nitrogen, was added dropwise 7-hydroxyindole (2.1 g, 15.7 mmol) in dimethylformamide (20 ml). After complete addition, the reaction was stirred at ambient temperature for 0.5 hour and then cooled to 15° C. To this cooled solution was added, dropwise, 1-bromo-3-chloropropane (2.5 g, 15.7 mmol) in dimethylformamide (5 ml). The reaction was then stirred at ambient temperature for 16 hours. The reaction was poured into water, and the aqueous suspension extracted with ethyl acetate. The ethyl acetate was washed with water, dried (MgSO4), and the solvent was concentrated to afford a dark brown oil. Following flash chromatography on silica gel, 7-(3-chloropropoxy)indole was obtained as a colorless oil, 1.0 g.

Aufarbeitung

  1. additionAfter complete addition
  2. temperaturecooled to 15° C
  3. additionTo this cooled solution was added
  4. stirringThe reaction was then stirred at ambient temperature for 16 hours
  5. extractionthe aqueous suspension extracted with ethyl acetate
  6. washThe ethyl acetate was washed with water
  7. dry with materialdried (MgSO4)
  8. concentrationthe solvent was concentrated
  9. customto afford a dark brown oil

Quellen und Nachweise

ORD-Eintrag
ord-58dfcecce32b4a2bab1b064832412dd3
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05652241

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