Potassium Carbonate → Isoflavone

HRID 402859

Reaction equation

HRID 402859 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+]>>[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

3

Reactant 2

HCID 11430Potassium CarbonateHCID 5280961Genistein

Product 1

HCID 72304IsoflavoneYield 63.2%

Conditions

Temperature
59 °C

Procedure

To a 100 mL round bottom flask was added genistein (500 mg, 1.85 mmol) and K2CO3 (1.02 g, 7.4 mmol). The flask was equipped with a reflux condenser and purged with N2. To the flask was added acetone (15 mL) and MeI (0.277 mL), and the reaction was heated to 59° C. Additional K2CO3 and MeI were added as needed to push the reaction. Upon completion, the reaction was allowed to cool to room temperature and was filtered to remove KI. Purified by flash column chromatography (SiO2, 2% MeOH/CH2Cl2) to afford 14 (260 mg, 45%) as an off-white solid. Analytical data for isoflavone 14: 1H NMR (500 MHz, CDCl3) δ 7.77 (s, 1H), 7.49 (d, J=9 Hz, 2H), 6.94 (d, J=9 Hz, 2H), 6.45 (s, 1H), 6.38 (s, 1H), 3.95 (s, 3H), 3.90 (s, 3H), 3.84 (s, 3H); 13C NMR (125 MHz, CDCl3) δ 175.7, 164.1, 161.7, 160.2, 159.6, 150.2, 130.6, 126.2, 124.6, 113.9, 110.2, 96.4, 92.7, 56.6, 56.0, 55.5; LCMS: Mass calculated for C18H16O5, [M+H]+, 313. Found 313.

Workup

  1. customThe flask was equipped with a reflux condenser
  2. custompurged with N2
  3. additionTo the flask was added acetone (15 mL) and MeI (0.277 mL)
  4. additionAdditional K2CO3 and MeI were added
  5. customthe reaction
  6. temperatureto cool to room temperature
  7. filtrationwas filtered
  8. customto remove KI
  9. customPurified by flash column chromatography (SiO2, 2% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-c81b3c1bf68d465fb4aaba3ca1af7cd0
Source dataset
uspto-grants-2014_06
Patent number
US08742141B2

Linked notes

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