(+/-)-3-Methyl-1-tribromomethyl-2-butenyl diazoacetate → 4-Tribromomethyl-6,6-dimethyl-2-oxo-3-oxabicyclo[3.1.0]hexane

HRID 127035

Reaktionsgleichung

Reaktionsgleichung von HRID 127035
[N+](=[CH:3][C:4]([O:6][CH:7]([C:12]([Br:15])([Br:14])[Br:13])[CH:8]=[C:9]([CH3:11])[CH3:10])=[O:5])=[N-]>C1(C)C=CC=CC=1.CC(CC(C)=O)=O.CC(CC(C)=O)=O.[Cu]>[Br:13][C:12]([Br:15])([Br:14])[CH:7]1[CH:8]2[CH:3]([C:9]2([CH3:11])[CH3:10])[C:4](=[O:5])[O:6]1

Komponenten

4

Edukt 1

HCID 53875604(+/-)-3-Methyl-1-tribromomethyl-2-butenyl diazoacetate

Produkt 1

HCID 125252254-Tribromomethyl-6,6-dimethyl-2-oxo-3-oxabicyclo[3.1.0]hexaneAusbeute 28 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 45052134Bis(pentane-2,4-dione-kappa~2~O~2~,O~4~)copperKatalysatorHCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

To a refluxing solution of cupric acetylacetonate (0.005 g, 0.019 mmole) in 40 ml of toluene was added dropwise over a period of 2.5 hours under an atmosphere of argon gas a solution of (±)-3-methyl-1-tribromomethyl-2-butenyl diazoacetate (0.203 g, 0.005 ml) in 10 ml of toluene. The mixture was then heated under reflux for one hour. After cooling, the reaction mixture was washed successively with two portions of 1 N aqueous hydrochloric acid, once with saturated aqueous sodium bicarbonate, and twice with saturated aqueous sodium chloride. After drying over magnesium sulfate, the solution was evaporated to give a yellow oil as the residue. The residue was purified by column chromatography on a silica gel column using 9/1 n-hexane/ethyl acetate as the eluent, yielding (±)-4-tribromomethyl-6,6-dimethyl-2-oxo-3-oxabicyclo[3.1.0]hexane (0.053 g, yield 28%); mp 101°-103° after recrystallization from n-hexane.

Aufarbeitung

  1. temperatureThe mixture was then heated
  2. temperatureunder reflux for one hour
  3. temperatureAfter cooling
  4. washthe reaction mixture was washed successively with two portions of 1 N aqueous hydrochloric acid, once with saturated aqueous sodium bicarbonate
  5. dry with materialAfter drying over magnesium sulfate
  6. customthe solution was evaporated
  7. customto give a yellow oil as the residue
  8. customThe residue was purified by column chromatography on a silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-addd5f4f14574345a8697c96a03c20a8
Quelldatensatz
uspto-grants-1981_03
Patentnummer
US04254282

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