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(+)-Camphorquinone → (1s,4r)-1,7,7-Trimethyl-3-[2-(5-methyl-1-phenyl-1h-pyrazol-4-yl)-2-oxo-eth-(e)-ylidene]-bicyclo[2.2.1]heptan-2-one

HRID 2243903
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2243903
COP([CH2:7][C:8]([C:10]1[CH:11]=[N:12][N:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:14]=1[CH3:15])=[O:9])(=O)OC.CC(C)([O-])C.[K+].[CH3:28][C@@:29]12[C:35]([CH3:37])([CH3:36])[C@@H:32]([CH2:33][CH2:34]1)[C:31](=O)[C:30]2=[O:39]>C(O)(C)(C)C>[CH3:28][C@@:29]12[C:35]([CH3:37])([CH3:36])[C@@H:32]([CH2:33][CH2:34]1)/[C:31](=[CH:7]\[C:8]([C:10]1[CH:11]=[N:12][N:13]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:14]=1[CH3:15])=[O:9])/[C:30]2=[O:39]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 1549179(+)-CamphorquinoneHCID 23665647Potassium tert-butoxideHCID 86609911[2-(5-Methyl-1-phenyl-1H-pyrazol-4-yl)-2-oxo-ethyl]-phosphonic acid dimethyl ester

Produkt 1

HCID 67364601(1s,4r)-1,7,7-Trimethyl-3-[2-(5-methyl-1-phenyl-1h-pyrazol-4-yl)-2-oxo-eth-(e)-ylidene]-bicyclo[2.2.1]heptan-2-oneAusbeute 74,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6386
tert-Butanol
Lösungsmittel

Versuchsvorschrift

[2-(5-Methyl-1-phenyl-1H-pyrazol-4-yl)-2-oxo-ethyl]-phosphonic acid dimethyl ester (1.1 g) in tert-butanol (60 mL) at RT under an argon atmosphere was treated with potassium tert-butoxide (0.412 g) and the mixture was stirred for 30 minutes. Then (1S,4R)-1,7,7-trimethyl-bicyclo[2.2.1]heptane-2,3-dione (0.499 g) was added at RT and the mixture was heated at reflux for 12 h under an argon atmosphere. The reaction mixture was partitioned between water and AcOEt, the layers were separated, the aqueous layer extracted twice with AcOEt. The combined organic layers were washed with water, dried over Na2SO4, filtered and evaporated. The residue was purified by flash chromatography (heptane/AcOEt 100% to 80%) to give (1S,4R)-1,7,7-trimethyl-3-[2-(5-methyl-1-phenyl-1H-pyrazol-4-yl)-2-oxo-eth-(E)-ylidene]-bicyclo[2.2.1]heptan-2-one (0.78 g) as a light yellow solid. MS (EI): 348.2 (M+).

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 12 h under an argon atmosphere
  3. customThe reaction mixture was partitioned between water and AcOEt
  4. customthe layers were separated
  5. extractionthe aqueous layer extracted twice with AcOEt
  6. washThe combined organic layers were washed with water
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was purified by flash chromatography (heptane/AcOEt 100% to 80%)

Quellen und Nachweise

ORD-Eintrag
ord-bf72ccea36c641bda136c57407615c01
Quelldatensatz
uspto-grants-2010_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07678795B2

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