2-Diazonio-1-[(3-methylbut-2-en-1-yl)oxy]ethen-1-olate → 6,6-Dimethyl-3-oxabicyclo[3.1.0]hexan-2-one

HRID 127041Notes

Reaction equation

HRID 127041 reaction equation
[N+](=[CH:3][C:4]([O:6][CH2:7][CH:8]=[C:9]([CH3:11])[CH3:10])=[O:5])=[N-]>O1CCOCC1.CC(CC(C)=O)=O.CC(CC(C)=O)=O.[Cu]>[CH3:10][C:9]1([CH3:11])[CH:3]2[CH:8]1[CH2:7][O:6][C:4]2=[O:5]

Participants

4

Reactant 1

HCID 544938542-Diazonio-1-[(3-methylbut-2-en-1-yl)oxy]ethen-1-olate

Product 1

HCID 118153586,6-Dimethyl-3-oxabicyclo[3.1.0]hexan-2-oneYield 75%

Reagents, catalysts & solvents 2

HCID 45052134Bis(pentane-2,4-dione-kappa~2~O~2~,O~4~)copperCatalystHCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 3-methyl-2-butenyl diazoacetate (41.3 mmole, 6.36 g) in dioxane (20 ml) was added dropwise to a refluxing solution of cupric acetylacetonate (1.03 mmole, 0.27 g) in dioxane (400 ml) over a period of 7 hours under an argon atmosphere. After completion of the addition, the reaction mixture was heated under reflux for 1 hour. The crude reaction mixture was distilled to afford (±)-6,6-dimethyl-2-oxo-3-oxabicyclo[3.1.0]hexane (3.85 g, 75% yield); bp 110°, 16 mm Hg.

Workup

  1. additionAfter completion of the addition
  2. temperaturethe reaction mixture was heated
  3. temperatureunder reflux for 1 hour
  4. customThe crude reaction mixture
  5. distillationwas distilled

Sources & evidence

ORD record
ord-9df1a84991f6429abf9be5e3d99e9b6a
Source dataset
uspto-grants-1981_03
Patent number
US04254282

Reaction notes

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