[C:1]1([C:7]2([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:11](=[O:12])[CH:10]=[CH:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl-].[Cl-].[Cl-].[Ce+3].[BH4-].[Na+].O>CO.C(Cl)Cl.C(O)C>[C:1]1([C:7]2([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:11]([OH:12])[CH:10]=[CH:9][CH2:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1
To a solution of 5,5-diphenyl-2-cyclopenten-1-one (1.0 g) and cerium trichloride 7 hydrate (1.59 g) in methanol (10 ml) and methylene chloride (4 ml) was added dropwise a solution of sodium borohydride (0.16 g) in ethanol (6 ml) at 0° C. to 3° C. To the reaction mixture, cerium trichloride 7 hydrate (0.80 g) and sodium borohydride (0.08 g) were added 4 times an hour. After the reaction finished, cold water (30 ml) was added, and the mixture was extracted with chloroform. The extract was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel with methylene chloride as an eluent to give 5,5-diphenyl-2-cyclopenten-1-ol 0.83 g).
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