Methyl iodide → HCID 14254520, compound

HRID 1905084Notes

Reaction equation

HRID 1905084 reaction equation
[Cl:1][C:2]1[C:7]2[C:8](=[O:19])[C:9]([C:12]3[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=3)=[CH:10][O:11][C:6]=2[CH:5]=[C:4]([O:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:3]=1.[C:27](=O)([O-])[O-].[K+].[K+].CI>CC(C)=O>[Cl:1][C:2]1[C:7]2[C:8](=[O:19])[C:9]([C:12]3[CH:13]=[CH:14][C:15]([O:18][CH3:27])=[CH:16][CH:17]=3)=[CH:10][O:11][C:6]=2[CH:5]=[C:4]([O:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 14254510HCID 14254510, compound

Product 1

HCID 14254520HCID 14254520, compoundYield 87.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In 150 ml of acetone was dissolved 5.5 g of ethyl {[5-chloro-3-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-7-yl]oxy}acetate under heating, and 4.8 g of anhydrous potassium carbonate was added thereto. To the solution was added 3.4 ml of methyl iodide, followed by refluxing for 2 hours. After cooling, the solvent was removed by distillation under reduced pressure. Water was added to the residue, and the insoluble material was extracted with ethyl acetate. The organic layer was dried over sodium sulfate and distilled under reduced pressure to remove the solvent. The residue was recrystallized from ethanol-chloroform to obtain 5.0 g of the entitled compound having a melting point of 121° to 122° C.

Workup

  1. temperatureunder heating
  2. temperatureby refluxing for 2 hours
  3. temperatureAfter cooling
  4. customthe solvent was removed by distillation under reduced pressure
  5. additionWater was added to the residue
  6. extractionthe insoluble material was extracted with ethyl acetate
  7. dry with materialThe organic layer was dried over sodium sulfate
  8. distillationdistilled under reduced pressure
  9. customto remove the solvent
  10. customThe residue was recrystallized from ethanol-chloroform

Sources & evidence

ORD record
ord-24e96c618c0d4497bf6d5d3376879ce2
Source dataset
uspto-grants-1989_06
Patent number
US04841076

Reaction notes

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