Pyridine → Dimefluthrin

HRID 1072121

反応式

HRID 1072121 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 213011Dimefluthrin収率 83.8%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ab590b1c1a6f4241bc6566d2c8dbf896
出典データセット
uspto-grants-2005_06
特許番号
US06908945B2

関連ノート

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