Pyridine → Dimefluthrin

HRID 1072121

반응식

HRID 1072121 반응식
[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]

참가 물질

5

반응물 3

HCID 1049PyridineHCID 26620(1R-trans)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarbonyl chlorideHCID 111721164-Methoxymethyl-2,3,5,6-tetrafluorobenzyl alcohol

생성물 1

HCID 213011Dimefluthrin수율 83.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ab590b1c1a6f4241bc6566d2c8dbf896
출처 데이터셋
uspto-grants-2005_06
특허 번호
US06908945B2

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