HCID 53809386, compound → HCID 12525246, compound

HRID 127038

Reaction equation

HRID 127038 reaction equation
[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

Participants

5

Reactant 1

HCID 53809386HCID 53809386, compound

Product 1

HCID 12525246HCID 12525246, compoundYield 96%

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 356OctaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

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°.

Workup

  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

Sources & evidence

ORD record
ord-db5419fa50ca48fe920bd1aa9b84a518
Source dataset
uspto-grants-1981_03
Patent number
US04254282

Linked notes

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