Ozone → HCID 14770294, compound

HRID 1382367Notes

Reaction equation

HRID 1382367 reaction equation
[CH3:1][O:2][CH2:3][CH:4]1[C:7](=[O:8])[O:6][CH:5]1[CH2:9][CH2:10][CH2:11][CH2:12][CH:13]([CH3:25])[CH2:14][C:15](C)=[CH:16]C(C)=CC(OC)=O.[O:26]=[O+][O-]>[Zn].C(O)(=O)C>[CH3:1][O:2][CH2:3][CH:4]1[C:7](=[O:8])[O:6][CH:5]1[CH2:9][CH2:10][CH2:11][CH2:12][CH:13]([CH3:25])[CH2:14][C:15](=[O:26])[CH3:16]

Participants

5

Reactant 2

HCID 24823OzoneHCID 54002481HCID 54002481, compound

Product 1

HCID 14770294HCID 14770294, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 400 mg (1.135 mmole) of methyl 11-(3-methoxymethyl-4-oxo-2-oxetanyl)3,5,7-trimethyl-2,4-undecadienoate in 10 ml of CHCl2 at -78° C., was bubbled ozone for 8 minutes. The resulting mixture was stirred for 30 minutes at -78° C. then at room temperature for another 30 minutes. Acetic acid and zinc dust were added. After stirring for 1 hour at room temperature, the solution was filtered and the filtrate was concentrated to dryness. The product was purified by flash column chromatography to give 8-(3-methoxymethyl-4-oxo-2-oxetanyl)-4-methyl-2-octanone as a colorless oil. ##STR20##

Workup

  1. waitat room temperature for another 30 minutes
  2. stirringAfter stirring for 1 hour at room temperature
  3. filtrationthe solution was filtered
  4. concentrationthe filtrate was concentrated to dryness
  5. customThe product was purified by flash column chromatography

Sources & evidence

ORD record
ord-5d0d353c1bfd45228598460f6734ddba
Source dataset
uspto-grants-1989_02
Patent number
US04806564

Reaction notes

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