Acetonitrile → N-[8-(2-Ethoxycarbonyl-5,6-dimethoxy-4,7-dioxoindan-2-yl)octanoyl]morpholine

HRID 2268514Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2268514
O=[N+]([O-])[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[Ce+4].[NH4+].[NH4+].C(#N)C.[CH2:31]([O:33][C:34]([C:36]1([CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][C:60]([N:62]2[CH2:67][CH2:66][O:65][CH2:64][CH2:63]2)=[O:61])[CH2:44][C:43]2[C:38](=[C:39]([O:51]C)[C:40]([O:49][CH3:50])=[C:41]([O:47][CH3:48])[C:42]=2[O:45]C)[CH2:37]1)=[O:35])[CH3:32]>O>[CH2:31]([O:33][C:34]([C:36]1([CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][C:60]([N:62]2[CH2:63][CH2:64][O:65][CH2:66][CH2:67]2)=[O:61])[CH2:37][C:38]2[C:39](=[O:51])[C:40]([O:49][CH3:50])=[C:41]([O:47][CH3:48])[C:42](=[O:45])[C:43]=2[CH2:44]1)=[O:35])[CH3:32]

Komponenten

5

Edukt 3

HCID 6342AcetonitrileHCID 180504Ceric ammonium nitrateHCID 18348513N-[8-(2-Ethoxycarbonyl-4,5,6,7-tetramethoxyindan-2-yl)octanoyl]morpholine

Produkt 1

HCID 18348585N-[8-(2-Ethoxycarbonyl-5,6-dimethoxy-4,7-dioxoindan-2-yl)octanoyl]morpholineAusbeute 57,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Versuchsvorschrift

A water (1.2 ml) solution of CAN (323 mg, 0.590 mmols) was dropwise added to an acetonitrile (2.5 ml) solution of N-[8-(2-ethoxycarbonyl-4,5,6,7-tetramethoxyindan-2-yl)octanoyl]morpholine (123 mg, 0.236 mmols) with cooling with ice and stirring was continued for 15 minutes. Water was added to the reaction mixture, which was then extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution and then dried. The solvent was evaporated out in vacuo and the resulting crude product was purified by silica gel column chromatography (hexane:ethyl acetate=2:1 to 1:1) to obtain the entitled compound (66.6 mg) as an oil.

Aufarbeitung

  1. temperaturewith cooling with ice
  2. extractionwas then extracted with ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  4. customdried
  5. customThe solvent was evaporated out in vacuo
  6. customthe resulting crude product was purified by silica gel column chromatography (hexane:ethyl acetate=2:1 to 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-0cfc01f3a44b4159bb27077f9f7c960a
Quelldatensatz
uspto-grants-2001_12
Patentnummer
US06326369B1

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