Chrysanthemic Acid → Dimefluthrin

HRID 1597384

Reaction equation

HRID 1597384 reaction equation
Cl.CN(C)CCCN=C=NCC.[CH3:13][O:14][CH2:15][C:16]1[C:23]([F:24])=[C:22]([F:25])[C:19]([CH2:20]O)=[C:18]([F:26])[C:17]=1[F:27].[CH3:28][C:29]([CH3:39])=[CH:30][CH:31]1[CH:33]([C:34]([OH:36])=[O:35])[C:32]1([CH3:38])[CH3:37]>C1(C)C=CC=CC=1>[CH3:28][C:29]([CH3:39])=[CH:30][CH:31]1[CH:33]([C:34]([O:36][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:35])[C:32]1([CH3:38])[CH3:37]

Participants

5

Reactant 3

HCID 2743Chrysanthemic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 111721164-Methoxymethyl-2,3,5,6-tetrafluorobenzyl alcohol

Product 1

HCID 213011Dimefluthrin

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride is added to a mixture of 4-methoxymethyl-2,3,5, 6-tetrafluorobenzyl alcohol, 3- (2-methyl-1-propenyl) -2, 2-dimethylcyclopropanecarboxylic acid {containing the stereoisomers in a ratio of (1R)-trans form: (1R)-cis form: (1S)-trans form: (1S)-cis form=49:49:1:1} and toluene under ice-cooling. The resulting mixture is heated to room temperature and stirred at room temperature. The reaction mixture is poured into ice water to be separated. The organic layer thus separated 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-dimethylcyclopropanecarboxylate (hereinafter referred to as the present compound 6).

Workup

  1. additioncontaining the stereoisomers in a ratio of (1R)-trans
  2. customform
  3. custom(1R)-cis form: (1S)-trans form
  4. customto be separated
  5. customThe organic layer thus separated
  6. washis washed with a saturated aqueous sodium chloride solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4c2b1488c86a49029414669cbf7f757b
Source dataset
uspto-grants-2001_09
Patent number
US06294576B1

Linked notes

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