Methyl iodide → Isoflavone

HRID 402861

Reaction equation

HRID 402861 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

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 5280961Genistein

Product 1

HCID 72304IsoflavoneYield 65.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Prepared according to the general procedure using genistein (500 mg, 1.85 mmol), K2CO3 (1.02 g, 7.4 mmol), acetone (15 mL) and MeI (0.277 mL). Purified by flash column chromatography (SiO2, 10% EtOAc/Hex) to afford 16 (270 mg, 49%) as an off-white solid. Analytical data for isoflavone 16: 1H NMR (500 MHz, CDCl3) δ 12.88 (s, 1H), 7.88 (s, 1H), 7.48 (d, J=8.5 Hz, 2H), 7.00 (d, J=9 Hz, 2H), 6.41 (d, J=8.5 Hz, 2H), 3.89 (s, 3H), 3.86 (s, 3H); 13C NMR (125 MHz, CDCl3) δ 181.1, 165.8, 163.0, 160.0, 158.2, 152.9, 130.4, 123.9, 123.2, 114.3, 106.5, 98.4, 92.7, 56.1, 55.6; LCMS: Mass calculated for C17H14O5, [M+H]+, 299. Found 299.

Workup

  1. customPrepared
  2. customPurified by flash column chromatography (SiO2, 10% EtOAc/Hex)

Sources & evidence

ORD record
ord-183c03df9a044d8fa716ee0031b12092
Source dataset
uspto-grants-2014_06
Patent number
US08742141B2

Linked notes

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