Water → (+/-)-alpha-(1-butyl-1H-imidazol-5-yl)-4-(3-chlorophenyl)-alpha-(4-chlorophenyl)-2-methoxy-6-quinolinemethanol

HRID 2229268Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2229268
C([Li])CCC.Br[C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[N:13]=[C:12]([O:17][CH3:18])[CH:11]=[C:10]2[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=1.[CH2:26]([N:30]1[C:34]([C:35]([C:37]2[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][CH:38]=2)=[O:36])=[CH:33][N:32]=[CH:31]1)[CH2:27][CH2:28][CH3:29].O>CCCCCC.C1COCC1>[CH2:26]([N:30]1[C:34]([C:35]([C:37]2[CH:38]=[CH:39][C:40]([Cl:43])=[CH:41][CH:42]=2)([C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[N:13]=[C:12]([O:17][CH3:18])[CH:11]=[C:10]3[C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=2)[OH:36])=[CH:33][N:32]=[CH:31]1)[CH2:27][CH2:28][CH3:29]

Komponenten

7

Edukt 4

HCID 962WaterHCID 120166726-Bromo-4-(3-chlorophenyl)-2-methoxyquinolineHCID 22714358(1-butyl-1H-imidazol-5-yl)(4-chlorophenyl)methanoneHCID 178418339Butyllithium

Produkt 1

HCID 22714345(+/-)-alpha-(1-butyl-1H-imidazol-5-yl)-4-(3-chlorophenyl)-alpha-(4-chlorophenyl)-2-methoxy-6-quinolinemethanolAusbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
-20 °C

Versuchsvorschrift

Butyllithium in hexane (1.6 M) (12.75 ml) was added dropwise at −20° C. under N2 to a solution of 6-bromo-4-(3-chlorophenyl)-2-methoxyquinoline (6.7 g) in THF (60 ml) and the mixture was stirred at −20° C. for 30 minutes. A solution of (1-butyl-1H-imidazol-5-yl)(4-chlorophenyl)methanone (3.35 g) in tetrahydrofuran (30 ml) was added at −20° C. under N2 and the mixture was stirred at room temperature for one night. Water was added and the mixture was extracted with ethyl acetate. The organic layer was dried (MgSO4), filtered off and evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 97/3/0.1). The pure fractions were collected and evaporated, yielding 2.5 g (total 48%) of (±)-α-(1-butyl-1H-imidazol-5-yl)-4-(3-chlorophenyl)-α-(4-chlorophenyl)-2-methoxy-6-quinolinemethanol (interm. 2).

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature for one night
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered off
  5. customevaporated
  6. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 97/3/0.1)
  7. customThe pure fractions were collected
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-1b7fe4f4a3df41c9b5a7429f1c1c0f25
Quelldatensatz
uspto-grants-2002_07
Patentnummer
US06420387B1

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