Pyridine → (2,3,5,6-tetrafluoro-4-methylphenyl)methyl(1R)-trans-2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate

HRID 1976307

반응식

HRID 1976307 반응식
[F:1][C:2]1[C:7]([F:8])=[C:6]([CH3:9])[C:5]([F:10])=[C:4]([F:11])[C:3]=1[CH2:12][OH:13].N1C=CC=CC=1.O1CCCC1.[CH3:25][C:26]1([CH3:36])[C@H:28]([CH:29]=[C:30]([CH3:32])[CH3:31])[C@H:27]1[C:33](Cl)=[O:34]>CCCCCC.C(OCC)(=O)C>[CH3:25][C:26]1([CH3:36])[C@H:28]([CH:29]=[C:30]([CH3:31])[CH3:32])[C@H:27]1[C:33]([O:13][CH2:12][C:3]1[C:2]([F:1])=[C:7]([F:8])[C:6]([CH3:9])=[C:5]([F:10])[C:4]=1[F:11])=[O:34]

참가 물질

6

반응물 4

HCID 1049PyridineHCID 8028TetrahydrofuranHCID 27342094-Methyl-2,3,5,6-tetrafluorobenzyl alcoholHCID 10867076(1R,3R)-2,2-Dimethyl-3-(2-methyl-1-propen-1-yl)cyclopropanecarbonyl chloride

생성물 1

HCID 11580987(2,3,5,6-tetrafluoro-4-methylphenyl)methyl(1R)-trans-2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate수율 87.1%

시약·촉매·용매 1

HCID 21226206Ethyl acetate hexane용매

실험 절차

To a mixture solution of 1.78 g of (2,3,5,6-tetrafluoro-4-methylphenyl)methanol, 0.87 g of pyridine and 20 ml of tetrahydrofuran, 2.06 g of (1R)-trans-2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylic chloride was added under ice-cooling and the mixture was stirred for 8 hours at room temperature. The reaction mixture was poured into about 100 ml of ice-water and extracted with each 100 ml of ethyl acetate twice. The combined ethyl acetate was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give a crude product, which was subjected to silica gel column chromatography (eluent: hexane/ethyl acetate=20/1) to give 2.75 g of (2,3,5,6-tetrafluoro-4-methylphenyl)methyl(1R)-trans-2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate (yield 87%).

후처리

  1. temperaturecooling
  2. extractionextracted with each 100 ml of ethyl acetate twice
  3. washThe combined ethyl acetate was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto give a crude product, which

출처 및 근거

ORD 기록
ord-1fb30dc999774aaf95acac4f309849c9
출처 데이터셋
uspto-grants-2001_05
특허 번호
US06225495B1

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