Ozone → 1,1-Dimethylethyl 6-formyl-2,2-dimethyl-1,3-dioxane-4-acetate

HRID 1085753Notes

Reaction equation

HRID 1085753 reaction equation
[O:1]=[O+][O-].[CH3:4][C:5]1([CH3:27])[O:10][CH:9]([CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH:7]([CH:19]=CC2C=CC=CC=2)[O:6]1>C(Cl)Cl>[CH:19]([CH:7]1[O:6][C:5]([CH3:4])([CH3:27])[O:10][CH:9]([CH2:11][C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13])[CH2:8]1)=[O:1]

Participants

4

Reactant 2

HCID 24823OzoneHCID 538002911,1-Dimethylethyl 2,2-dimethyl-6-(2-phenylethenyl)-1,3-dioxane-4-acetate

Product 1

HCID 156146011,1-Dimethylethyl 6-formyl-2,2-dimethyl-1,3-dioxane-4-acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ozone was bubbled into a solution of 1,1-dimethylethyl 2,2-dimethyl-6-(2-phenylethenyl)-1,3-dioxane-4-acetate (3.0 g, 9 mmol) in 100 mL of methylene chloride at -78° C. until a blue color persisted. Nitrogen was then bubbled into the solution without cooling until the color disappeared. The temperature had risen to -20° C. Methyl sulfide (3 mL) was added and the solution stirred for 18 hours. The solvent was removed in vacuo and the residue purified by chromatography on silica eluting with 20% ethyl acetate in hexane to give 1.78 g of the title compound. Recrystallization from pentane gave the compound as a white solid; m.p.=71-73° C.

Workup

  1. customNitrogen was then bubbled into the solution
  2. temperaturewithout cooling until the color
  3. customhad risen to -20° C
  4. additionMethyl sulfide (3 mL) was added
  5. customThe solvent was removed in vacuo
  6. customthe residue purified by chromatography on silica eluting with 20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-db7d4bcf5bc94f5bb6d3cf7f2e6cdb18
Source dataset
uspto-grants-1991_04
Patent number
US05010205

Reaction notes

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