Potassium Fluoride → HCID 86641940, Verbindung

HRID 384110Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 384110
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:4][N:3]=1.C([Sn](CCCC)(CCCC)/[CH:28]=[CH:29]/[C:30]([O:32][CH2:33][CH3:34])=[O:31])CCC.[F-].[K+]>CN(C)C=O.O>[O:16]([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[CH2:9][O:8][C:5]1[CH:6]=[CH:7][C:2](/[CH:28]=[CH:29]/[C:30]([O:32][CH2:33][CH3:34])=[O:31])=[N:3][CH:4]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Komponenten

6

Edukt 3

HCID 522689Potassium FluorideHCID 10949132HCID 10949132, VerbindungHCID 86641939HCID 86641939, Verbindung

Produkt 1

HCID 86641940HCID 86641940, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of 2-bromo-5-((2-phenoxybenzyl)oxy)pyridine (1.0 g) in dimethylformamide (7 ml), 1.26 g of ethyl (2E)-3-(tributylstannyl)acrylate and 350 mg of tetrakis triphenylphosphine palladium were added, and the reaction solution was stirred overnight at 100° C. under nitrogen atmosphere. The reaction solution was cooled, then 15 ml of a saturated aqueous potassium fluoride solution was added, and the reaction solution was stirred for 1 hour, followed by removing insoluble matters by filtration through Celite and the filtrate was concentrated under reduced pressure. The residue obtained was diluted with water, extracted with diethyl ether, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue obtained was purified by silica gel column chromatography (eluent: ethyl acetate/hexane (0:100-25:75-30:70)) to afford the title compound as a yellow solid.

Aufarbeitung

  1. temperatureThe reaction solution was cooled
  2. stirringthe reaction solution was stirred for 1 hour
  3. customby removing insoluble matters
  4. filtrationby filtration through Celite
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue obtained
  7. extractionextracted with diethyl ether
  8. dry with materialdried over magnesium sulfate
  9. distillationThe solvent was distilled off under reduced pressure
  10. customthe residue obtained
  11. customwas purified by silica gel column chromatography (eluent: ethyl acetate/hexane (0:100-25:75-30:70))

Quellen und Nachweise

ORD-Eintrag
ord-e75affcb75b54169ab0a899643dd84ce
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367708B2

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