Ozone → 2,2-Dimethyl-3-(2-oxopropyl)cyclopropanecarbaldehyde

HRID 2285802Notes

Reaction equation

HRID 2285802 reaction equation
CN(C)C=[CH:4][CH:5]1[CH:7]([CH2:8][C:9](=[O:11])[CH3:10])[C:6]1([CH3:13])[CH3:12].[O:15]=[O+][O-]>C(Cl)Cl>[CH3:12][C:6]1([CH3:13])[CH:7]([CH2:8][C:9](=[O:11])[CH3:10])[CH:5]1[CH:4]=[O:15]

Participants

4

Reactant 2

HCID 24823OzoneHCID 545240321-(3-(2-(Dimethylamino)ethenyl)-2,2-dimethylcyclopropyl)-2-propanone

Product 1

HCID 114691882,2-Dimethyl-3-(2-oxopropyl)cyclopropanecarbaldehydeYield 84.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution 2.4 g of 1-(3-(2-(dimethylamino)ethenyl)-2,2-dimethylcyclopropyl)-2-propanone, the product of Embodiment I, in 50 ml of methylene chloride was added 0.6 g of ozone over 20 min at -80° C. The resulting mixture was purged with air and 1.5 g of triethylamine was added dropwise at -30° C. The resulting mixture, after stirring and warming to room temperature, had a negative test to starch iodide paper. The reaction mixture was poured into 25 ml 1 N hydrochloride acid solution. The resulting mixture separated into two phases and the methylene chloride phase was washed with water, dried with MgSO4, filtered and stripped to yield 1.6 g of the desired product as an oil.

Workup

  1. customThe resulting mixture was purged with air and 1.5 g of triethylamine
  2. additionwas added dropwise at -30° C
  3. additionThe reaction mixture was poured into 25 ml 1 N hydrochloride acid solution
  4. customThe resulting mixture separated into two phases
  5. washthe methylene chloride phase was washed with water
  6. dry with materialdried with MgSO4
  7. filtrationfiltered

Sources & evidence

ORD record
ord-b47f1aa6469f4241ab34d5243bcfcccf
Source dataset
uspto-grants-1982_04
Patent number
US04324915

Reaction notes

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