Chrysanthemic Acid → Dimefluthrin

HRID 1597383ノート

反応式

HRID 1597383 の反応式
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]

参加物

5

反応物 3

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

生成物 1

HCID 213011Dimefluthrin

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-14046e01eb5a4d76bf8146335bb1d5fc
出典データセット
uspto-grants-2001_09
特許番号
US06294576B1

反応ノート

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