Water → HCID 23157283, Verbindung

HRID 507919Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 507919
[H-].[Na+].[Br:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][C:5]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[CH2:19]([O:21][CH2:22][CH2:23]Cl)[CH3:20].O>CN(C)C=O>[Br:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]([CH2:20][CH2:19][O:21][CH2:22][CH3:23])[C:5]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 12341Ethane, 1-chloro-2-ethoxy-HCID 24758Sodium hydrideHCID 231573293-Bromo-2-phenyl-1H-indole

Produkt 1

HCID 23157283HCID 23157283, VerbindungAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Under ice-cooling, sodium hydride (60% in oil, 0.48 g, 12.0 mmol) was added to a solution of 3-bromo-2-phenyl-1H-indole (2.72 g, 10.0 mmol) in N,N-dimethylformamide (10 mL) by small portions, and the mixture was stirred under a nitrogen atmosphere at the same temperature for 30 min. To the reaction mixture was added 2-chloroethyl ethyl ether (1.65 mL, 15.0 mmol), and the mixture was stirred at 70° C. for 3 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-25% ethyl acetate/hexane) to give the title compound (2.60 g, yield 76%) as a red oil.

Aufarbeitung

  1. temperatureUnder ice-cooling
  2. stirringthe mixture was stirred at 70° C. for 3 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (hexane-25% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-f421684a2eb14aa2acc8514bf54df247
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07786165B2

Notizen zur Reaktion

Wird geladen…