Acetonitrile → Ethyl 2-[4-(4-ethoxycarbonyl-1-oxabutyl)phenyl]-5,6-dimethoxy-4,7-dioxo-2-indancarboxylate

HRID 2268521Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2268521
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]([CH2:36][CH2:37][CH2:38][O:39][C:40]1[CH:45]=[CH:44][C:43]([C:46]2([C:63]([O:65][CH2:66][CH3:67])=[O:64])[CH2:54][C:53]3[C:48](=[C:49]([O:61]C)[C:50]([O:59][CH3:60])=[C:51]([O:57][CH3:58])[C:52]=3[O:55]C)[CH2:47]2)=[CH:42][CH:41]=1)=[O:35])[CH3:32]>O>[CH2:31]([O:33][C:34]([CH2:36][CH2:37][CH2:38][O:39][C:40]1[CH:45]=[CH:44][C:43]([C:46]2([C:63]([O:65][CH2:66][CH3:67])=[O:64])[CH2:54][C:53]3[C:52](=[O:55])[C:51]([O:57][CH3:58])=[C:50]([O:59][CH3:60])[C:49](=[O:61])[C:48]=3[CH2:47]2)=[CH:42][CH:41]=1)=[O:35])[CH3:32]

Komponenten

5

Edukt 3

HCID 6342AcetonitrileHCID 180504Ceric ammonium nitrateHCID 18348634Ethyl 2-[4-(4-ethoxycarbonyl-1-oxabutyl)phenyl]-4,5,6,7-tetramethoxy-2-indancarboxylate

Produkt 1

HCID 15552354Ethyl 2-[4-(4-ethoxycarbonyl-1-oxabutyl)phenyl]-5,6-dimethoxy-4,7-dioxo-2-indancarboxylateAusbeute 70,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Versuchsvorschrift

A water (1.0 ml) solution of CAN (795 mg, 1.45 mmols) was dropwise added to an acetonitrile (6.0 ml) solution of ethyl 2-[4-(4-ethoxycarbonyl-1-oxabutyl)phenyl]-4,5,6,7-tetramethoxy-2-indancarboxylate (300 mg, 0.581 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 water and a saturated aqueous sodium chloride solution and then dried. The solvent was evaporated in vacuo, and the resulting crude product was purified by silica gel column chromatography (hexane:ethyl acetate=10:1 to 5:1) to obtain the entitled compound (200 mg) as an oil.

Aufarbeitung

  1. temperaturewith cooling with ice
  2. extractionwas then extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materiala saturated aqueous sodium chloride solution and then dried
  5. customThe solvent was evaporated in vacuo
  6. customthe resulting crude product was purified by silica gel column chromatography (hexane:ethyl acetate=10:1 to 5:1)

Quellen und Nachweise

ORD-Eintrag
ord-e6425c0388a54fa59f61fd1882c2eeef
Quelldatensatz
uspto-grants-2001_12
Patentnummer
US06326369B1

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