Methyl iodide → Kampferol-3,4'-dimethyl ether

HRID 2222318Notes

Reaction equation

HRID 2222318 reaction equation
C[C@@H]1O[C@@H](OC[C@H]2O[C@@H]([O:16][C:17]3[CH:22]=[C:21]4[O:23][C:24]([C:28]5[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[C:30](O)[CH:29]=5)=[CH:25][C:26](=[O:27])[C:20]4=[C:19]([OH:37])[CH:18]=3)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O.[C:44](=O)([O-])[O-:45].[K+].[K+].IC.C(OCC)(=O)C>CN(C)C=O.ClCCl>[OH:37][C:19]1[CH:18]=[C:17]([OH:16])[CH:22]=[C:21]2[C:20]=1[C:26](=[O:27])[CH:25]=[C:24]([C:28]1[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[C:30]([O:45][CH3:44])[CH:29]=1)[O:23]2

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 5281613Diosmin

Product 1

HCID 5351234Kampferol-3,4'-dimethyl etherYield 82.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
90 °C

Procedure

1 kg of 3′,5,7-trihydroxy-4′-methoxy flavone-7-rutinoside and 454 g of potassium carbonate were dissolved in dimethylformamide at 10° C., which was heated and stirred at 90° C. for 8 hours. The reaction solution was cooled to room temperature. To the solution was added 1 kg of iodomethane, followed by stirring at room temperature for 12 hours. Upon completing the reaction, 50 L of mixed solution of ethyl acetate and dichloromethane (3:2) was added thereto. The resultant solution was stirred for 30 minutes and then filtered. 5.2 L of methanol and 5 kg of conc. hydrochloric acid were added to the filtered solid, followed by heating to reflux at 65° C. for 8 hours. The reaction mixture was cooled down to room temperature. The precipitated solid were collected by filtration and washed with a small amount of methanol to give a desired compound (yellow solid, 426 g, yield: 82%).

Workup

  1. temperaturewhich was heated
  2. temperatureThe reaction solution was cooled to room temperature
  3. stirringby stirring at room temperature for 12 hours
  4. additionwas added
  5. filtrationfiltered
  6. addition5.2 L of methanol and 5 kg of conc. hydrochloric acid were added to the filtered solid
  7. temperatureby heating
  8. temperatureto reflux at 65° C. for 8 hours
  9. temperatureThe reaction mixture was cooled down to room temperature
  10. filtrationThe precipitated solid were collected by filtration
  11. washwashed with a small amount of methanol

Sources & evidence

ORD record
ord-98d530cc048545f9a9766039912edb51
Source dataset
uspto-grants-2008_05
Patent number
US07371775B2

Reaction notes

Loading…