Hydrochloric Acid → HCID 91354131, Verbindung

HRID 72281Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 72281
[CH:1]12[CH2:8][CH:5]([CH2:6][CH2:7]1)[C:4](=[O:9])[CH2:3][C:2]2=[O:10].C1(C)C=CC=CC=1.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[CH3:30][C:31]1[C:36]([Pb+3])=[C:35]([CH3:38])[CH:34]=[C:33]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH:32]=1.Cl>C(Cl)(Cl)Cl.CN(C)C1C=CN=CC=1>[CH3:30][C:31]1[C:36]([CH:3]2[C:4](=[O:9])[CH:5]3[CH2:8][CH:1]([CH2:7][CH2:6]3)[C:2]2=[O:10])=[C:35]([CH3:38])[CH:34]=[C:33]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH:32]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 144686Bicyclo(3.2.1)octane-2,4-dioneHCID 178476522HCID 178476522, Verbindung

Produkt 1

HCID 91354131HCID 91354131, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

To a mixture of bicyclo[3.2.1]octane-2,4-dione (0.553 g, 4 mmol) in dry chloroform (12 ml) is added 4-dimethylaminopyridine (2.44 g, 20 mmol), and the mixture is stirred at room temperature until all the solid is dissolved. To this solution is then added dry toluene (8 ml), and 3,5-dimethylbiphen-4-yllead triacetate (0.5 M solution in dry chloroform, 10 ml, 5 mmol), and the mixture is heated under reflux for 1 hour. The reaction mixture is cooled to room temperature, acidified to pH=1 with 2N aqueous hydrochloric acid, filtered and the filtrate is extracted with dichloromethane. The organic extracts are combined, dried over anhydrous magnesium sulfate, filtered and the filtrate evaporated in vacuo. The residue is further purified by column chromatography on silica gel to give 3-(3,5-dimethylbiphen-4-yl)bicyclo[3.2.1]octane-2,4-dione as a white powder.

Aufarbeitung

  1. dissolutionis dissolved
  2. temperaturethe mixture is heated
  3. temperatureunder reflux for 1 hour
  4. temperatureThe reaction mixture is cooled to room temperature
  5. filtrationfiltered
  6. extractionthe filtrate is extracted with dichloromethane
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customthe filtrate evaporated in vacuo
  10. customThe residue is further purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-293d5728408042508f8c05665f2ea7c8
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08828908B2

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