Pyridine → Dimefluthrin

HRID 1072121

Reaction equation

HRID 1072121 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[C:11]([F:12])=[C:10]([F:13])[C:7]([CH2:8][OH:9])=[C:6]([F:14])[C:5]=1[F:15].N1C=CC=CC=1.[CH3:22][C:23]([CH3:33])=[CH:24][CH:25]1[CH:27]([C:28](Cl)=[O:29])[C:26]1([CH3:32])[CH3:31]>O1CCCC1>[CH3:22][C:23]([CH3:33])=[CH:24][CH:25]1[CH:27]([C:28]([O:9][CH2:8][C:7]2[C:6]([F:14])=[C:5]([F:15])[C:4]([CH2:3][O:2][CH3:1])=[C:11]([F:12])[C:10]=2[F:13])=[O:29])[C:26]1([CH3:32])[CH3:31]

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 83.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 10 ml of tetrahydrofuran, 1.0 g of 4-methoxymethy-2,3,5,6-tetrafluorobenzyl alcohol and 0.42 g of pyridine were dissolved, 0.9 g of 3-(2-methyl-1-propenyl)-2,2-dimethylcyclopropanecarboxylic chloride {stereoisomers ratio (1R)-trans:(1R)-cis:(1S)-trans:(1S)-cis=93.9:2.5:3.5:0.1} was added thereto and stirred for 8 hours at room temperature. After that, the reaction mixture was poured into about 50 ml of ice-water and extracted with 80 ml of ethyl acetate twice. The combined organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 1.4 g of 4-methoxymethy-2,3,5,6-tetrafluorobenzyl 3-(2-methyl-1-propenyl)-2,2-dimethylcyclopropane-carboxylate.

Workup

  1. extractionextracted with 80 ml of ethyl acetate twice
  2. washThe combined organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ab590b1c1a6f4241bc6566d2c8dbf896
Source dataset
uspto-grants-2005_06
Patent number
US06908945B2

Linked notes

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