Acetyl chloride → HCID 11687955, Verbindung

HRID 252497

Reaktionsgleichung

Reaktionsgleichung von HRID 252497
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)[CH:7]=[CH:6]2.[Al](Cl)(CC)CC.[C:26](Cl)(=[O:28])[CH3:27]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)[CH:7]=[C:6]2[C:26](=[O:28])[CH3:27]

Komponenten

5

Edukt 3

HCID 6367Acetyl chlorideHCID 7277Diethylaluminum chlorideHCID 59426158HCID 59426158, Verbindung

Produkt 1

HCID 11687955HCID 11687955, VerbindungAusbeute 71,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

5-Methoxy-1-(4-methoxyphenyl)-1-H-indole (50 mg, 0.2 mmol), prepared by the method of example 1C, is dissolved in 1 mL of CH2Cl2 at 0° C. Et2AlCl (300 μL, 1M in hexanes, 0.3 mmol) is then added. After stirring at 0° C. for 30 min, a solution of acetyl chloride (22 mL, 0.3 mmol) in 1 mL of CH2Cl2 is added dropwise. This is stirred at 0° C. for a further 90 min. The reaction mixture is quenched with H2O and is extracted with CH2Cl2 and concentrated in vacuo. Purification by column chromatography on silica gel EtOAc/CH2Cl2 (5/95) yields the title compound as a white solid (42 mg, 71%).

Aufarbeitung

  1. stirringThis is stirred at 0° C. for a further 90 min
  2. customThe reaction mixture is quenched with H2O
  3. extractionis extracted with CH2Cl2
  4. concentrationconcentrated in vacuo
  5. customPurification by column chromatography on silica gel EtOAc/CH2Cl2 (5/95)

Quellen und Nachweise

ORD-Eintrag
ord-1132071910f5494f9a19b338630207be
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07868037B2

Verknüpfte Notizen

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