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

HRID 1901121Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1901121
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.C[Mg+].[Br-].[CH2:20]1COCC1.[NH4+].[Cl-]>CCOCC.Cl[Ni]Cl.O.C1(C)C=CC=CC=1>[O:14]1[CH:15]=[CH:16][C:12]([C:6]2[C:5]3[C:10](=[CH:11][C:2]([CH3:20])=[CH:3][CH:4]=3)[N:9]=[CH:8][CH:7]=2)=[CH:13]1

Komponenten

9

Edukt 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 233701707-Chloro-4-(furan-3-yl)quinolineHCID 178418689HCID 178418689, Verbindung

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 24385Nickel DichlorideKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a mixture of 7-chloro-4-(3-furyl)quinoline (30.2 g) and NiCl2 (dppp) (7.1 g) in Et2O (950 mL) was added MeMgBr (141 mL of a 1.4M solution 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. customThe layers were separated
  3. extractionthe aqueous phase was extracted with EtOAc
  4. washThe combined organics were washed with NH4OAc buffer, brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-7370116fc9a84715ad717391f22689a5
Quelldatensatz
uspto-grants-1996_11
Patentnummer
US05576338

Notizen zur Reaktion

Wird geladen…