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Potassium Hydroxide → HCID 22112797, Verbindung

HRID 564720
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 564720
Br[C:2]1[O:12][C:5]2=[C:6]([O:10][CH3:11])[N:7]=[CH:8][CH:9]=[C:4]2[CH:3]=1.C(B(CC)[C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)C.[OH-].[K+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd]>[CH3:11][O:10][C:6]1[N:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[C:2]([C:16]3[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=3)[O:12][C:5]=12
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 14797Potassium HydroxideHCID 6428513-(Diethylboryl)pyridineHCID 22112801HCID 22112801, Verbindung

Produkt 1

HCID 22112797HCID 22112797, VerbindungAusbeute 50,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 67553Tetrabutylammonium IodideKatalysator
HCID 11979704
Tetrakis(triphenylphosphine)palladium
Katalysator
HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

2-Bromo-7-methoxyfuro[2,3-c]pyridine (0.6 g), diethyl(3-pyridyl)borane (0.387 g), tetrakis(triphenylphosphine)palladium(O) (0.157 g), potassium hydroxide (0.442 g) and tetrabutyl ammonium iodide (0.486 g) were combined in dry tetrahydrofuran (25 ml) under dry nitrogen. The mixture was heated to reflux for 1 hour. The solvent was removed in vacuo, and the residue partitioned between dichloromethane (20 ml) and water (20 ml). The aqueous layer was extracted with dichloromethane (20 ml). The combined organics were washed with water (24×40 ml), dried over magnesium sulfate, filtered and the solvent removed in vacuo. Purification by column chromatography on silica eluting with 2:1 heptane:ethyl acetate gave the title compound (0.30 g) as a white solid.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 1 hour
  3. customThe solvent was removed in vacuo
  4. customthe residue partitioned between dichloromethane (20 ml) and water (20 ml)
  5. extractionThe aqueous layer was extracted with dichloromethane (20 ml)
  6. washThe combined organics were washed with water (24×40 ml)
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customthe solvent removed in vacuo
  10. customPurification by column chromatography on silica eluting with 2:1 heptane

Quellen und Nachweise

ORD-Eintrag
ord-8d7c0c025dfc4f988aa8c774c5b8ca39
Quelldatensatz
uspto-grants-2001_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06169090A

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