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Potassium Carbonate → HCID 66778260, Verbindung

HRID 2091355
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2091355
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([OH:8])[C:3]=1[C:9](=O)[CH3:10].C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][C:20]([CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1)=[O:21]>CN(C)C=O>[CH:22]1([C:20]([C:19]2[O:8][C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[C:3]=3[C:9]=2[CH3:10])=[O:21])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 27373242'-Fluoro-6'-hydroxyacetophenoneHCID 111600272-Bromo-1-cyclohexylethanone

Produkt 1

HCID 66778260HCID 66778260, VerbindungAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution (50 mL) of 1-(2-fluoro-6-hydroxyphenyl)ethanone (2.5 g) in N,N-dimethylformamide were added potassium carbonate (6.7 g) and 2-bromo-1-cyclohexylethanone (4.0 g) synthesized in Example A51(1) at room temperature, and the mixture was stirred at room temperature for 16 hr. The reaction mixture was allowed to cool to room temperature and filtered through celite. Water was added to the filtrate, and the mixture was extracted with diethyl ether. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained residue was dissolved in N,N-dimethylformamide (50 mL) again, 1,8-diazabicyclo[5.4.0]undec-7-ene (2.6 mL) was added to the solution, and the mixture was stirred at 110° C. for 1 hr with heating. After cooling to room temperature, the reaction mixture was quenched with 1N hydrochloric acid, and the reaction mixture was extracted with diethyl ether. The extract was concentrated under reduced pressure, and the precipitated compound was recrystallized from diisopropyl ether-hexane to give the title object compound (2.6 g, 62%) as a colorless solid.

Aufarbeitung

  1. customsynthesized in Example A51(1) at room temperature
  2. temperatureto cool to room temperature
  3. filtrationfiltered through celite
  4. additionWater was added to the filtrate
  5. extractionthe mixture was extracted with diethyl ether
  6. washThe extract was washed with saturated brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. dissolutionThe obtained residue was dissolved in N,N-dimethylformamide (50 mL) again
  10. addition1,8-diazabicyclo[5.4.0]undec-7-ene (2.6 mL) was added to the solution
  11. stirringthe mixture was stirred at 110° C. for 1 hr
  12. temperaturewith heating
  13. temperatureAfter cooling to room temperature
  14. customthe reaction mixture was quenched with 1N hydrochloric acid
  15. extractionthe reaction mixture was extracted with diethyl ether
  16. concentrationThe extract was concentrated under reduced pressure
  17. customthe precipitated compound was recrystallized from diisopropyl ether-hexane

Quellen und Nachweise

ORD-Eintrag
ord-c6d9716e1cf04c92a75e1380459dfa4b
Quelldatensatz
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08436043B2

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