HCID 53809386, Verbindung → HCID 12525246, Verbindung

HRID 127038

Reaktionsgleichung

Reaktionsgleichung von HRID 127038
[N+](=[C:3]([C:8]([O:10][CH:11]([C:16]([Cl:19])([Cl:18])[Cl:17])[CH:12]=[C:13]([CH3:15])[CH3:14])=[O:9])[C:4]([O:6][CH3:7])=[O:5])=[N-]>CCCCCCCC.C(OCC)(=O)C.[Cu]>[Cl:17][C:16]([Cl:19])([Cl:18])[CH:11]1[CH:12]2[C:3]([C:4]([O:6][CH3:7])=[O:5])([C:13]2([CH3:15])[CH3:14])[C:8](=[O:9])[O:10]1

Komponenten

5

Edukt 1

HCID 53809386HCID 53809386, Verbindung

Produkt 1

HCID 12525246HCID 12525246, VerbindungAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23978CopperKatalysatorHCID 356OctaneLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a refluxing suspension of copper powder (6.6 g, 0.104 mole) in 320 ml of n-octane was added dropwise in one hour a solution of methyl (±)-3-methyl-1-trichloromethyl-2-butenyl diazomalonate (6.6 g, 0.02 mole, prepared as described above for the ethyl ester) in 80 ml of n-octane. The reaction mixture was heated for 21/2 hours under reflux and then filtered while hot. The n-octane was evaporated from the filtrate under vacuum to produce a residue which was dissolved in ethyl acetate. The solution was washed successively with aqueous 1 N hydrochloric acid, aqueous sodium bicarbonate, and aqueous sodium chloride. After drying the solution over magnesium sulfate, the ethyl acetate was removed by evaporation, yielding methyl (±)-4-trichloromethyl-6,6-dimethyl-2-oxo-3-oxabicyclo[3.1.0]-hexane-1-carboxylate (5.77 g, 96% yield) as an oil. Trituration of the oil with ether afforded the crystalline lactone; mp, 118°-120°.

Aufarbeitung

  1. customprepared
  2. temperatureThe reaction mixture was heated for 21/2 hours
  3. temperatureunder reflux
  4. filtrationfiltered while hot
  5. customThe n-octane was evaporated from the filtrate under vacuum
  6. customto produce a residue which
  7. washThe solution was washed successively with aqueous 1 N hydrochloric acid, aqueous sodium bicarbonate, and aqueous sodium chloride
  8. dry with materialAfter drying the solution over magnesium sulfate
  9. customthe ethyl acetate was removed by evaporation

Quellen und Nachweise

ORD-Eintrag
ord-db5419fa50ca48fe920bd1aa9b84a518
Quelldatensatz
uspto-grants-1981_03
Patentnummer
US04254282

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