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

HRID 1976307

Reaktionsgleichung

Reaktionsgleichung von HRID 1976307
[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]

Komponenten

6

Edukt 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

Produkt 1

HCID 11580987(2,3,5,6-tetrafluoro-4-methylphenyl)methyl(1R)-trans-2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylateAusbeute 87,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21226206Ethyl acetate hexaneLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-1fb30dc999774aaf95acac4f309849c9
Quelldatensatz
uspto-grants-2001_05
Patentnummer
US06225495B1

Verknüpfte Notizen

Wird geladen…