Ozone → HCID 9859217, compound

HRID 1195402Notes

Reaction equation

HRID 1195402 reaction equation
[CH3:1][O:2][C:3](=[O:21])[CH2:4][C@H:5]1[CH2:10][C@@H:9]([CH:11]=CC2C=CC=CC=2)[O:8][C:7]([CH3:20])([CH3:19])[O:6]1.[O:22]=[O+][O-]>CO>[CH3:20][C:7]1([CH3:19])[O:6][CH:5]([CH2:4][C:3]([O:2][CH3:1])=[O:21])[CH2:10][CH:9]([CH:11]=[O:22])[O:8]1

Participants

4

Reactant 2

HCID 24823OzoneHCID 53926402HCID 53926402, compound

Product 1

HCID 9859217HCID 9859217, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Cis-2,2-dimethyl-6-(2-phenylethenyl)-1,3-dioxane-4-acetic acid methyl ester (prepared in Example 133) was dissolved in methanol (10 mL) and ozone was passed through the solution at -78° C. until the color of the solution turned blue. The reaction mixture was purged with nitrogen to remove excess ozone then dimethyl sulfide was added and the temperature was allowed to warm up to room temperature. The reaction was evaporated in vacuo and the residual oil was purified by chromatography on silica gel using diethyl ether-hexane (3:1) as the eluent to afford the title compound.

Workup

  1. customwas passed through the solution at -78° C. until the color of the solution
  2. customThe reaction mixture was purged with nitrogen
  3. customto remove excess ozone
  4. additiondimethyl sulfide was added
  5. customThe reaction was evaporated in vacuo
  6. customthe residual oil was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-45924f1018e24cab9d6f1d92407b6c1a
Source dataset
uspto-grants-1992_05
Patent number
US05110940

Reaction notes

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