Furan → 1-{[2-(2-chlorophenyl)-1-(4-chlorophenyl)-1H-imidazol-4-yl]carbonyl}-4-(2-furyl)-4-piperidinol
Reaktionsgleichung
[Li]CCCC.[O:6]1[CH:10]=[CH:9][CH:8]=[CH:7]1.[Cl:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]1[N:19]([C:32]2[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=2)[CH:20]=[C:21]([C:23]([N:25]2[CH2:30][CH2:29][C:28](=[O:31])[CH2:27][CH2:26]2)=[O:24])[N:22]=1.[NH4+].[Cl-]>C1COCC1.O>[Cl:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]1[N:19]([C:32]2[CH:33]=[CH:34][C:35]([Cl:38])=[CH:36][CH:37]=2)[CH:20]=[C:21]([C:23]([N:25]2[CH2:26][CH2:27][C:28]([C:7]3[O:6][CH:10]=[CH:9][CH:8]=3)([OH:31])[CH2:29][CH2:30]2)=[O:24])[N:22]=1Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- -78 °C
Versuchsvorschrift
BuLi (0.875 mL, 1.40 mmol, 1 M solution in THF) was added slowly to a solution of furan (0.106 mL, 1.45 mmol) in THF (2 mL) at −78° C., and the mixture was stirred at −78° C. for 1 h. A solution of 1-{[2-(2-chlorophenyl)-1-(4-chlorophenyl)-1H-imidazol-4-yl]carbonyl}-4-piperidinone (0.3 g, 0.68 mmol) in THF (1 mL) was added slowly. The mixture was stirred at −78° C. for 2 h and saturated NH4Cl (3 mL) and water added. The mixture was extracted with ethyl acetate (3×20 mL) and dried over MgSO4. The product (0.142 g, 61%) was isolated by column (ethyl acetate). MS (Electrospray) 482 (M)+; 1H NMR (300 MHz, CD2Cl2) δ .7.85 (s, 1H), 7.51-7.31 (m, 7H), 7.10-6.98 (m, 4H), 7.17-7.10 (m, 2H), 6.39 (s, 1H), 6.29 (s, 1H), 4.68 (br, 1H), 4.28 (br, 1H), 3.94 (br, 1H), 3.57 (br, 1H), 2.26-1.91 (m, 4H).
Aufarbeitung
- stirringThe mixture was stirred at −78° C. for 2 h
- extractionThe mixture was extracted with ethyl acetate (3×20 mL)
- dry with materialdried over MgSO4
Quellen und Nachweise
- ORD-Eintrag
- ord-7808f4fc5c7343d9a96c341e882c51cf
- Quelldatensatz
- uspto-grants-2005_11
- Patentnummer
- US06960601B2
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