Acetone → HCID 178467978, compound

Reaction equation

C1COCC1.[NH:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[NH:8][C:7]1=[C:15]([C:26]([C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([F:34])[CH:29]=1)=[O:27])[C:16]([C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=1)[CH:21]=[O:22])=[O:17].[Cl-].[NH4+].[CH3:37][C:38]([CH3:40])=[O:39]>>[NH:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[NH:8][C:7]1=[C:15]([C:16]([C:18]1[CH:25]=[CH:24][CH:23]=[C:20]([CH:21]([OH:22])[CH2:37][C:38](=[O:39])[CH3:40])[CH:19]=1)=[O:17])[C:26]([C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([F:34])[CH:29]=1)=[O:27]

Participants

Reactant 4

HCID 180Acetone

HCID 8028Tetrahydrofuran

HCID 25517Ammonium Chloride

HCID 178519574HCID 178519574, compound

Product 1

HCID 178467978HCID 178467978, compoundYield 53%

Procedure

At −78° C., 1.0 M sodium hexamethylenedisilazane-THF solution was added dropwise to 10 ml of THF solution containing 300 mg of 3-[2-(1,3-dihydro-2H-benzimidazol-2-ylidene)-3-(3-fluorophenyl)-3-oxopropanoyl]benzaldehyde and 69 μl of acetone and stirred for 15 minutes. This was mixed with 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 184 mg (53%) of 2-(1,3-dihydro-2H-benzimidazol-2-ylidene)-1-(3-fluorophenyl)-3-[3-(1-hydroxy-3-oxobutyl)phenyl]propane-1,3-dione (Reference Example 7-1) from a hexane-ethyl acetate (2:1-1:2) eluate. ES+: 445