Dimethylformamide → (2,3,5,6-tetrafluoro-4-methylphenyl)methyl(1RS)-trans-2,2-dimethyl-3-((E)-1-propenyl)cyclopropanecarboxylate

HRID 1976311ノート

反応式

HRID 1976311 の反応式
[CH3:1][C:2]1([CH3:11])[C@@H:4](/[CH:5]=[CH:6]/[CH3:7])[C@@H:3]1[C:8]([OH:10])=[O:9].Br[CH2:13][C:14]1[C:19]([F:20])=[C:18]([F:21])[C:17]([CH3:22])=[C:16]([F:23])[C:15]=1[F:24].CN(C)C=O.C(N(CC)CC)C>O>[CH3:11][C:2]1([CH3:1])[C@@H:4](/[CH:5]=[CH:6]/[CH3:7])[C@@H:3]1[C:8]([O:10][CH2:13][C:14]1[C:15]([F:24])=[C:16]([F:23])[C:17]([CH3:22])=[C:18]([F:21])[C:19]=1[F:20])=[O:9]

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 27783681-Bromomethyl-4-methyl-2,3,5,6-tetrafluorobenzeneHCID 86756669(1RS)-trans-2,2-dimethyl-3-((E)-1-propenyl)cyclopropanecarboxylic acid

生成物 1

HCID 86756668(2,3,5,6-tetrafluoro-4-methylphenyl)methyl(1RS)-trans-2,2-dimethyl-3-((E)-1-propenyl)cyclopropanecarboxylate収率 90%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
80 °C

実験手順

To a mixture solution of 0.50 g of (1RS)-trans-2,2-dimethyl-3-((E)-1-propenyl)cyclopropanecarboxylic acid, 0.72 g of 1-bromomethyl-2,3,5,6-tetrafluoro-4-methylbenzene and 8 ml of dimethylformamide, 1.0 g of triethylamine was added and the mixture was stirred at 80° C. for 4 hours. After the mixture was cooled to room temperature, water was poured into the mixture and the mixture was extracted with diethyl ether. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (eluent: hexane/ethyl acetate=20/1) to give 0.83 g of (2,3,5,6-tetrafluoro-4-methylphenyl)methyl(1RS)-trans-2,2-dimethyl-3-((E)-1-propenyl)cyclopropanecarboxylate

後処理

  1. temperatureAfter the mixture was cooled to room temperature
  2. extractionthe mixture was extracted with diethyl ether
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-024bda9c046d4a68a0512bd78260a400
出典データセット
uspto-grants-2001_05
特許番号
US06225495B1

反応ノート

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