Tetrahydrofuran → 4-Methoxymethy-2,3,5,6-tetrafluorobenzyl 3-formyl-2,2-dimethylcyclopropanecarboxylate

HRID 1072122

Reaction equation

HRID 1072122 reaction equation
[O:1]1CCCC1.O1CCOCC1.CC(C)=[CH:14][CH:15]1[CH:17]([C:18]([O:20][CH2:21][C:22]2[C:27]([F:28])=[C:26]([F:29])[C:25]([CH2:30][O:31][CH3:32])=[C:24]([F:33])[C:23]=2[F:34])=[O:19])[C:16]1([CH3:36])[CH3:35].I([O-])(=O)(=O)=O.[Na+]>[Os](=O)(=O)(=O)=O.O>[CH:14]([CH:15]1[CH:17]([C:18]([O:20][CH2:21][C:22]2[C:23]([F:34])=[C:24]([F:33])[C:25]([CH2:30][O:31][CH3:32])=[C:26]([F:29])[C:27]=2[F:28])=[O:19])[C:16]1([CH3:36])[CH3:35])=[O:1]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 312751,4-DioxaneHCID 213011DimefluthrinHCID 23667635Sodium periodate

Product 1

HCID 129939974-Methoxymethy-2,3,5,6-tetrafluorobenzyl 3-formyl-2,2-dimethylcyclopropanecarboxylate

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent2×

Procedure

To a mixture of 25 ml of tetrahydrofuran and 150 ml of 1,4-dioxane, 15.4 g of 4-methoxymethy-2,3,5,6-tetrafluorobenzyl 3-(2-methyl-1-propenyl)-2,2-dimethylcyclopropanecarboxylate (prepared by the method described above) were dissolved and 1.0 g of osmium tetraoxide was added thereto at room temperature. Further, 50 ml of water containing 24.0 g of sodium metaperiodate were added thereto and refluxed for 2 hours under heating. After that, the reaction mixture was poured into about 200 ml of water and extracted with 200 ml of ethyl acetate twice. The combined organic layer was washed with 1% aqueous sodium thiosulfate solution, saturated aqueous sodium hydrogencarbonate solution and saturated brine, subsequently, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 10.4 g of 4-methoxymethy-2,3,5,6-tetrafluorobenzyl 3-formyl-2,2-dimethylcyclopropanecarboxylate.

Workup

  1. customprepared by the method
  2. dissolutionwere dissolved
  3. customat room temperature
  4. temperaturerefluxed for 2 hours
  5. temperatureunder heating
  6. extractionextracted with 200 ml of ethyl acetate twice
  7. washThe combined organic layer was washed with 1% aqueous sodium thiosulfate solution, saturated aqueous sodium hydrogencarbonate solution and saturated brine
  8. dry with materialsubsequently, dried over anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-65c3f8d749df4fa8bf0572aee3f0504c
Source dataset
uspto-grants-2005_06
Patent number
US06908945B2

Linked notes

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