Methyl iodide → Isoflavone

Reaction equation

[CH:1]1[C:6]([C:7]2[C:16](=[O:17])[C:15]3[C:14](O)=[CH:13][C:12](O)=[CH:11][C:10]=3[O:9][CH:8]=2)=[CH:5][CH:4]=[C:3](O)[CH:2]=1.C([O-])([O-])=O.[K+].[K+].CI>CC(C)=O>[O:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:16](=[O:17])[C:7]([C:6]2[CH:1]=[CH:2][CH:3]=[CH:4][CH:5]=2)=[CH:8]1

Participants

Procedure

Prepared according to the general procedure using genistein (300 mg, 1.11 mmol), K2CO3 (307 mg, 2.22 mmol), acetone and MeI (0.139 mL). Purified by flash column chromatography (SiO2, 1% MeOH/CH2Cl2) to afford 15 (70 mg, 22%) as an off-white solid. Analytical data for isoflavone 15: 1H NMR (500 MHz, DMSO) δ 12.96 (s, 1H), 9.62 (s, 1H), 8.41 (s, 1H), 7.39 (d, J=8.5 Hz, 2H), 6.82 (d, J=8.5 Hz, 2H), 6.65 (s, 1H), 6.41 (s, 1H), 3.86 (s, 3H); 13C NMR (125 MHz, DMSO) δ 181.1, 165.9, 162.4, 158.2, 158.1, 155.1, 130.9, 123.2, 121.7, 115.8, 106.1, 98.7, 93.1, 56.8; LCMS: Mass calculated for C16H12O5, [M+H]+, 285. Found 285.