Sodium borohydride → 2-(1,3-dihydrobenzimidazol-2-ylidene)-1-[3-(1,3-dihydroxybutyl)phenyl]-3-(3-fluorophenyl)propane-1,3-dione
Reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]1=[C:10]([C:20]([C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([CH:28]([OH:33])[CH2:29][C:30](=[O:32])[CH3:31])[CH:23]=1)=[O:21])[C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=1)=[O:12].[BH4-].[Na+]>C(O)C>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]1=[C:10]([C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=1)=[O:12])[C:20]([C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([CH:28]([OH:33])[CH2:29][CH:30]([OH:32])[CH3:31])[CH:23]=1)=[O:21]Participants
4
Procedure
At −10° C., 10 ml of ethanol solution containing 184 mg of 2-(1,3-dihydro-2H-benzimidazol-2-ylidene)-1-(3-fluorophenyl)-3-[3-(1-hydroxy-3-oxobutyl)phenyl]propane-1,3-dione was mixed with sodium borohydride and stirred for 30 minutes. This was appropriate amounts of saturated ammonium chloride aqueous solution and purified water, extracted with ethyl acetate and dried with anhydrous magnesium sulfate. After concentration, the thus formed residue was purified by a silica gel column chromatography to obtain 110 mg (60%) of 2-(1,3-dihydro-2H-benzimidazol-2-ylidene)-1-[3-(1,3-dihydroxybutyl)phenyl]-3-(3-fluorophenyl)propane-1,3-dione (Example 6-1) from a hexane-ethyl:acetate (1:1-1:3) eluate.