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Acetonitrile → Ethyl 2-(4-benzyloxyphenyl)-5,6-dimethoxy-4,7-dioxo-2-indancarboxylate

HRID 2268520
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2268520
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:38][C:39]1[CH:44]=[CH:43][C:42]([C:45]2([C:62]([O:64][CH2:65][CH3:66])=[O:63])[CH2:53][C:52]3[C:47](=[C:48]([O:60]C)[C:49]([O:58][CH3:59])=[C:50]([O:56][CH3:57])[C:51]=3[O:54]C)[CH2:46]2)=[CH:41][CH:40]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>O>[CH2:31]([O:38][C:39]1[CH:40]=[CH:41][C:42]([C:45]2([C:62]([O:64][CH2:65][CH3:66])=[O:63])[CH2:46][C:47]3[C:48](=[O:60])[C:49]([O:58][CH3:59])=[C:50]([O:56][CH3:57])[C:51](=[O:54])[C:52]=3[CH2:53]2)=[CH:43][CH:44]=1)[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 6342AcetonitrileHCID 180504Ceric ammonium nitrateHCID 18348586Ethyl 2-(4-benzyloxyphenyl)-4,5,6,7-tetramethoxy-2-indancarboxylate

Produkt 1

HCID 15552353Ethyl 2-(4-benzyloxyphenyl)-5,6-dimethoxy-4,7-dioxo-2-indancarboxylateAusbeute 54,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962
Water
Lösungsmittel
2×

Versuchsvorschrift

A water (1.0 ml) solution of CAN (976 mg, 1.78 mmols) was dropwise added to an acetonitrile (7.0 ml) solution of ethyl 2-(4-benzyloxyphenyl)-4,5,6,7-tetramethoxy-2-indancarboxylate (350 mg, 0.711 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=5:1) followed by recrystallization from hexane-ethyl acetate to obtain the entitled compound (178 mg) as crystals.

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=5:1)
  7. customfollowed by recrystallization from hexane-ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-3af06506c80f456ba4a389ae5b5055a9
Quelldatensatz
uspto-grants-2001_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06326369B1

Notizen zur Reaktion

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