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Acetonitrile → 4-[4-(5,6-Dimethoxy-4,7-dioxoindan-2-yl)butoxy]phenylmethanol

HRID 2268523
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2268523
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.C[O:32][C:33]1[C:41]([O:42][CH3:43])=[C:40]([O:44][CH3:45])[C:39]([O:46]C)=[C:38]2[C:34]=1[CH2:35][CH:36]([CH2:48][CH2:49][CH2:50][CH2:51][O:52][C:53]1[CH:58]=[CH:57][C:56]([CH2:59][OH:60])=[CH:55][CH:54]=1)[CH2:37]2>O>[CH3:43][O:42][C:41]1[C:33](=[O:32])[C:34]2[CH2:35][CH:36]([CH2:48][CH2:49][CH2:50][CH2:51][O:52][C:53]3[CH:58]=[CH:57][C:56]([CH2:59][OH:60])=[CH:55][CH:54]=3)[CH2:37][C:38]=2[C:39](=[O:46])[C:40]=1[O:44][CH3:45]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 6342AcetonitrileHCID 180504Ceric ammonium nitrateHCID 18348611HCID 18348611, Verbindung

Produkt 1

HCID 183486414-[4-(5,6-Dimethoxy-4,7-dioxoindan-2-yl)butoxy]phenylmethanolAusbeute 43,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Versuchsvorschrift

A water (1.0 ml) solution of CAN (1.24 g, 2.27 mmols) was dropwise added to an acetonitrile (8.0 ml) solution of 4-[4-(4,5,6,7-tetramethoxyindan-2-yl)butoxy]phenylmethanol (370 mg, 0.888 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 out in vacuo, and the resulting crude product was purified by silica gel column chromatography (hexane:ethyl acetate=10:1 to 2:1) followed by recrystallization (from hexane-ethyl acetate) to obtain the entitled compound (150 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 out in vacuo
  6. customthe resulting crude product was purified by silica gel column chromatography (hexane:ethyl acetate=10:1 to 2:1)
  7. customfollowed by recrystallization (from hexane-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-67ce911d53884dc8bc4add837e3d6d1b
Quelldatensatz
uspto-grants-2001_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06326369B1

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