Water → 4-(Furan-3-yl)-7-methylquinoline

HRID 741838Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 741838
Cl[C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:12]3[CH:16]=[CH:15][O:14][CH:13]=3)=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.[CH3:17][Mg+].[Br-].[NH4+].[Cl-].O>CCOCC.Cl[Ni]1(Cl)[P](C2C=CC=CC=2)(C2C=CC=CC=2)CCC[P]1(C1C=CC=CC=1)C1C=CC=CC=1>[O:14]1[CH:15]=[CH:16][C:12]([C:6]2[C:5]3[C:10](=[CH:11][C:2]([CH3:17])=[CH:3][CH:4]=3)[N:9]=[CH:8][CH:7]=2)=[CH:13]1

Komponenten

7

Edukt 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 233701707-Chloro-4-(furan-3-yl)quinolineHCID 178418689HCID 178418689, Verbindung

Produkt 1

HCID 233701774-(Furan-3-yl)-7-methylquinoline

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418745HCID 178418745, VerbindungKatalysatorHCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
30 °C

Versuchsvorschrift

To a mixture of 7-chloro-4-(furan-3-yl)quinoline (30.2 g) and [1,3-bis(diphenylphosphino)propane]nickel (II) chloride (7.1 g) in Et2O (950 mL) was added MeMgBr (141 mL, 1.4M in 3:1 THF:toluene) at such a rate to maintain a temperature of 30° C. The mixture was refluxed for 30 min., cooled to 0° C. and saturated NH4Cl (200 mL) was added followed by H2O (100 mL). The layers were separated and the aqueous phase was extracted with EtOAc. The combined organics were washed with NH4OAc buffer, brine, dried (MgSO4) and concentrated. Chromatography (silica gel;EtOAc/hexane (3:7)) provided the title compound as a beige oil.

Aufarbeitung

  1. temperatureThe mixture was refluxed for 30 min.
  2. temperaturecooled to 0° C.
  3. customThe layers were separated
  4. extractionthe aqueous phase was extracted with EtOAc
  5. washThe combined organics were washed with NH4OAc buffer, brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-07cefc43d8834002ad853d126d18dce2
Quelldatensatz
uspto-grants-1996_09
Patentnummer
US05552437

Notizen zur Reaktion

Wird geladen…