[CH:1]1[C:6]([C:7]2[C:16](=[O:17])[C:15]3[CH:14]=[CH:13][C:12]([OH:18])=[CH:11][C:10]=3[O:9][CH:8]=2)=[CH:5][CH:4]=[C:3]([OH:19])[CH:2]=1.C([O-])=O.[NH4+].C(Cl)Cl.CCOC(C)=O.CCOCC.CCCCCC>CO.[Pd]>[CH2:8]1[O:9][C:10]2[CH:11]=[C:12]([OH:18])[CH:13]=[CH:14][C:15]=2[C:16](=[O:17])[CH:7]1[C:6]1[CH:1]=[CH:2][C:3]([OH:19])=[CH:4][CH:5]=1
To a solution of daidzein (0.657 g, 2.58 mmol) in methanol (60 mL) was added 10% Pd/C (0.657 g) carefully, following by ammonium formate (0.652 g, 10.3 mmol). The mixture was heated up to 50-60° C. and stirred for one hour. The reaction was monitored by TLC (CH2Cl2/EtOAc=7:2 or 70% Et2O/Hexane) and GC. After the reaction complete, the Pd/C was filtered and the filtrate was concentrated, which gave a crude product (0.558 g) of dihydrodaidzein as the major product and the trans/cis isomers of tetrahydrodaidzein as the minor products. The dihydrodaidzein was purified by standard procedures.
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