Pyridine → Dimefluthrin

HRID 1597385Notes

Reaction equation

HRID 1597385 reaction equation
[CH3:1][C:2]([CH3:12])=[CH:3][CH:4]1[CH:6]([C:7](Cl)=[O:8])[C:5]1([CH3:11])[CH3:10].[CH3:13][O:14][CH2:15][C:16]1[C:23]([F:24])=[C:22]([F:25])[C:19]([CH2:20][OH:21])=[C:18]([F:26])[C:17]=1[F:27].N1C=CC=CC=1>O1CCCC1>[CH3:1][C:2]([CH3:12])=[CH:3][CH:4]1[CH:6]([C:7]([O:21][CH2:20][C:19]2[C:18]([F:26])=[C:17]([F:27])[C:16]([CH2:15][O:14][CH3:13])=[C:23]([F:24])[C:22]=2[F:25])=[O:8])[C:5]1([CH3:11])[CH3:10]

Participants

5

Reactant 3

HCID 1049PyridineHCID 26620(1R-trans)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarbonyl chlorideHCID 111721164-Methoxymethyl-2,3,5,6-tetrafluorobenzyl alcohol

Product 1

HCID 213011Dimefluthrin

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-(2-methyl-1-propenyl)-2,2-dimethylcyclopropanecarboxylic acid chloride {containing the stereoisomers in a ratio of (1R)-trans form: (1R)-cis form: (1S)-trans form: (1S)-cis form=76:19:4:1} is added to a mixture of 4-methoxymethyl-2,3,5,6-tetrafluorobenzyl alcohol, pyridine and tetrahydrofuran under ice-cooling. The resulting mixture is heated to room temperature and stirred at room temperature. The reaction mixture is poured into ice water and extracted with ethyl acetate. The combined ethyl acetate layer is washed with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The resultant residue is subjected to silica gel column chromatography to obtain 4-methoxymethyl-2,3,5,6-tetrafluorobenzyl 3-(2-methyl-1-propenyl)-2,2-dimethylcyclopropane-carboxylate (hereinafter referred to as the present compound 7).

Workup

  1. customform
  2. custom(1R)-cis form: (1S)-trans form
  3. temperaturecooling
  4. extractionextracted with ethyl acetate
  5. washThe combined ethyl acetate layer is washed with a saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bf93215353994b1bb2e468d60690e77e
Source dataset
uspto-grants-2001_09
Patent number
US06294576B1

Reaction notes

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