1-Methylimidazole → HCID 10297355, compound

Participants

Reaction Conditions

Reaction Steps

BuLi 1.6M (20.6 ml) was added dropwise at −70° C. under N2 flow to a mixture of 1-methyl-1H-imidazole (0.033 mol) in THF (60 ml). The mixture was stirred at −70° C. for 30 min. chlorotriethyl-silane (0.033 mol) was added. The mixture was brought slowly to 10° C. and cooled again to −70° C. BuLi 1.6M (20.6 ml) was added dropwise. The mixture was stirred at −70° C. for 1 hour, brought to −15° C. and cooled again to −70° C. A suspension of intermediate 27 (0.022 mol) in THF (80 ml) was added dropwise. The mixture was stirred at −70° C. for 30 min, then brought to room temperature, hydrolized, extracted with EtOAc and decanted. The organic layer was dried (MgSO4), filtered and the solvent was evaporated till dryness. The residue (13 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 95/5/0.2; 20–45 μm). One pure fraction was collected and the solvent evaporated. The residue was crystallized from CH3CN and diethyl ether. The precipitate was filtered off and dried, yielding 1.2 g (12.2%) of 4-(3-chlorophenyl)-6-[3-furanylhydroxy(1-methyl-1H-imidazol-5-yl)methyl]-1-methyl-2(1H)-quinolinone, melting point 248° C.

Provenance & Evidence