Pyridine → Dimefluthrin

HRID 1597380

Reaction equation

HRID 1597380 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 213011DimefluthrinYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.90 Gram of 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=93.9:2.5:3.5:0.1} was added to a mixture of 1.0 g of 4-methoxymethyl-2,3,5,6-tetrafluorobenzyl alcohol, 0.42 g of pyridine and 10 ml of tetrahydrofuran under ice-cooling. The resulting mixture was heated to room temperature and stirred at room temperature for 8 hours. The reaction mixture was poured into about 50 ml of ice water and extracted twice with 80 ml of ethyl acetate. The combined ethyl acetate layer was washed with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The resultant residue was subjected to silica gel column chromatography to obtain 1.40 g (yield: 84%) of 4-methoxymethyl-2,3,5,6-tetrafluorobenzyl 3-(2-methyl-1-propenyl)-2,2-dimethylcyclopropanecarboxylate (hereinafter referred to as the present compound 1).

Workup

  1. customform
  2. custom(1R)-cis form: (1S)-trans form
  3. temperaturecooling
  4. extractionextracted twice with 80 ml of ethyl acetate
  5. washThe combined ethyl acetate layer was 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-2a2c1e3a435d4b488f3fcfa15ab52811
Source dataset
uspto-grants-2001_09
Patent number
US06294576B1

Linked notes

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