Acetic Anhydride → HCID 23552950, Verbindung

HRID 2270971Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2270971
[Cl-].[Al+3].[Cl-].[Cl-].[C:5](OC(=O)C)(=[O:7])[CH3:6].[Cl:12][CH2:13][C:14]([O:16][C:17]1[CH:25]=[C:24]2[C:20]([CH:21]=[CH:22][N:23]2[C:26](=[O:31])[C:27]([CH3:30])([CH3:29])[CH3:28])=[CH:19][CH:18]=1)=[O:15]>ClC(Cl)C>[C:5]([C:21]1[C:20]2[C:24](=[CH:25][C:17]([O:16][C:14](=[O:15])[CH2:13][Cl:12])=[CH:18][CH:19]=2)[N:23]([C:26](=[O:31])[C:27]([CH3:28])([CH3:30])[CH3:29])[CH:22]=1)(=[O:7])[CH3:6]

Komponenten

5

Edukt 3

HCID 7918Acetic AnhydrideHCID 6451240Aluminum(III) ChlorideHCID 103796646-chloroacetoxy-1-pivaloylindole

Produkt 1

HCID 23552950HCID 23552950, VerbindungAusbeute 36 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 63651,1-DichloroethaneLösungsmittel2×

Versuchsvorschrift

To a suspension of 9.5 g (72 mmol) of aluminum chloride in dichloroethane (47.5 ml) was added dropwise 3.64 g (36 mmol) of acetic anhydride. After stirring for 15 min at room temperature, to the above mixture was added dropwise 3.3 g (11 mmol) of 6-chloroacetoxy-1-pivaloylindole (prepared in accordance with the literature (SYNTHESIS, p1018, 1994) in dichloroethane (33 ml). After stirring for 1 hour at room temperature, the mixture was poured into ice-water. The mixture was extracted with ethyl acetate. The extract was washed twice with water and aqueous sodium bicarbonate, and dried. The solution was concentrated and the obtained residue was chromatographed on silica gel (ethyl acetate as eluant) to give 1.23 g of 3-acetyl-6-chloroacetoxy-1-pivaloylindole as an oil. Yield: 36%.

Aufarbeitung

  1. stirringAfter stirring for 1 hour at room temperature
  2. extractionThe mixture was extracted with ethyl acetate
  3. washThe extract was washed twice with water and aqueous sodium bicarbonate
  4. customdried
  5. concentrationThe solution was concentrated
  6. customthe obtained residue was chromatographed on silica gel (ethyl acetate as eluant)

Quellen und Nachweise

ORD-Eintrag
ord-764eef94fac04de694931c6140c15e5e
Quelldatensatz
uspto-grants-2001_12
Patentnummer
US06333323B1

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