Ozone → HCID 14724059, compound

HRID 1195400Notes

Reaction equation

HRID 1195400 reaction equation
[O:1]=[O+][O-].[CH:4]([CH:9]1[O:14][C:13]2([CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[O:12][CH:11]([CH2:20][C:21]([OH:23])=[O:22])[CH2:10]1)=CC=CC>C(Cl)Cl>[CH:4]([CH:9]1[O:14][C:13]2([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]2)[O:12][CH:11]([CH2:20][C:21]([OH:23])=[O:22])[CH2:10]1)=[O:1]

Participants

4

Reactant 2

HCID 24823OzoneHCID 54553066HCID 54553066, compound

Product 1

HCID 14724059HCID 14724059, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ozone was passed through a solution of 4-(1,3-pentadienyl)-1,5-dioxaspiro[5.5]undecane-2-acetic acid (570 mg, 2.0 mmol) in methylene chloride (25 mL) at -78° C. After the solution had attained a blue color, nitrogen was passed through the solution to remove the excess ozone. Dimethyl sulfide (0.5 mL) was added and the solution was concentrated under reduced pressure to afford the title compound as a viscous oil which was used without further purification in the subsequent step.

Workup

  1. customto remove the excess ozone
  2. additionDimethyl sulfide (0.5 mL) was added
  3. concentrationthe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-375ace2257e84db7b25bff65c6c932bc
Source dataset
uspto-grants-1992_05
Patent number
US05110940

Reaction notes

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