HCID 54224365, compound → HCID 10538220, compound

HRID 127034

Reaction equation

HRID 127034 reaction equation
[N+](=[CH:3][C:4]([O:6][C@@H:7]([C:12]([Cl:15])([Cl:14])[Cl:13])[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])[C@H:3]2[C@@H:8]1[C@H:7]([C:12]([Cl:15])([Cl:14])[Cl:13])[O:6][C:4]2=[O:5]

Participants

4

Reactant 1

HCID 54224365HCID 54224365, compound

Product 1

HCID 10538220HCID 10538220, compoundYield 90%

Reagents, catalysts & solvents 2

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

Procedure

A solution of (1R)-3-methyl-1-trichloromethyl-2-butenyl diazoacetate (0.90 g, 3.33 mmole) from Example IA.4.(a) in 15 ml of dry dioxane was added dropwise over a period of 2.6 hours to a catalytic amount (approximately 2 mole %) of cupric acetylacetonate in 65 ml of refluxing dry dioxane under a nitrogen atmosphere. After refluxing for an additional hour, the mixture was evaporated, and an etheral solution of the residue was washed with 1 N HCl, saturated NaHCO3, and saturated NaCl, then dried over MgSO4 and evaporated to give (1R,4R,5S)-6,6-dimethyl-2-oxo-4-trichloromethyl-3-oxabicyclo[3.1.0]hexane (0.73 g, 90% crude yield) as a green-yellow oil.

Workup

  1. temperatureAfter refluxing for an additional hour
  2. customthe mixture was evaporated
  3. washan etheral solution of the residue was washed with 1 N HCl, saturated NaHCO3, and saturated NaCl
  4. dry with materialdried over MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-c0357354741542c28358447386ef9bb0
Source dataset
uspto-grants-1981_03
Patent number
US04254282

Linked notes

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