Chrysanthemic Acid → Dimefluthrin

HRID 1597383

Reaktionsgleichung

Reaktionsgleichung von HRID 1597383
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]>O1CCCC1>[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]

Komponenten

5

Edukt 3

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

Produkt 1

HCID 213011Dimefluthrin

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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=99:0:1:0} 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-dimethylcyclopropanecarboxylate (hereinafter referred to as the present compound 5).

Aufarbeitung

  1. additioncontaining the stereoisomers in a ratio of (1R)-trans
  2. customform
  3. custom(1R)-cis form: (1S)-trans form
  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

Quellen und Nachweise

ORD-Eintrag
ord-14046e01eb5a4d76bf8146335bb1d5fc
Quelldatensatz
uspto-grants-2001_09
Patentnummer
US06294576B1

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