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

HRID 1976311노트

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HRID 1976311 반응식
[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]

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

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온도
80 °C

실험 절차

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

후처리

  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

출처 및 근거

ORD 기록
ord-024bda9c046d4a68a0512bd78260a400
출처 데이터셋
uspto-grants-2001_05
특허 번호
US06225495B1

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