Ethanol → HCID 22995924, Verbindung

HRID 1167187

Reaktionsgleichung

Reaktionsgleichung von HRID 1167187
C1COCC1.[C:6]1([Li])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH3:13][C:14]1[CH:15]=[N:16][C:17]2[C:22]([CH:23]=1)=[CH:21][CH:20]=[CH:19][C:18]=2[O:24][CH3:25].C(O)C>CCCCCC.C1(C)C=CC=CC=1>[C:6]1([C:15]2[C:14]([CH3:13])=[CH:23][C:22]3[C:17](=[C:18]([O:24][CH3:25])[CH:19]=[CH:20][CH:21]=3)[N:16]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Komponenten

7

Edukt 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 139842868-Methoxy-3-methylquinolineHCID 178506676HCID 178506676, Verbindung

Produkt 1

HCID 22995924HCID 22995924, VerbindungAusbeute 35 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

84 ml of anhydrous THF and 42 ml of a 2M solution of phenyllithium in hexane are placed in a 1 l triple-necked flask cooled to 0° C. with an ice bath. The reaction medium is heated to 65° C. and a solution of 12 g (69 mmol) of 3-methyl-8-methoxyquinoline in 50 ml of toluene is added dropwise. The mixture is brought to reflux for 6 h and cooled to ambient temperature, and 50 ml of ethanol are added dropwise. The mixture is concentrated under vacuum and the residue is purified by silica gel chromatography (eluent: heptane/ethyl acetate 9/1) to provide 5.9 g of 2-phenyl-3-methyl-8-methoxyquinoline. (Yield: 35%)

Aufarbeitung

  1. temperatureThe reaction medium is heated to 65° C.
  2. temperatureto reflux for 6 h
  3. temperaturecooled to ambient temperature
  4. concentrationThe mixture is concentrated under vacuum
  5. customthe residue is purified by silica gel chromatography (eluent: heptane/ethyl acetate 9/1)

Quellen und Nachweise

ORD-Eintrag
ord-bd8978060d004a369e3f40e6c373427a
Quelldatensatz
uspto-grants-2003_09
Patentnummer
US06617336B1

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