Methyl iodide → HCID 59264719, compound

HRID 646532Notes

Reaction equation

HRID 646532 reaction equation
IC.[CH2:3]([O:5][C:6]([C:8]1[O:9][C:10]2[C:15]([C:16](=[O:25])[C:17]=1[C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=1)=[CH:14][C:13]([CH2:26][CH3:27])=[C:12]([OH:28])[CH:11]=2)=[O:7])[CH3:4].[C:29](=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:3]([O:5][C:6]([C:8]1[O:9][C:10]2[C:15]([C:16](=[O:25])[C:17]=1[C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=1)=[CH:14][C:13]([CH2:26][CH3:27])=[C:12]([O:28][CH3:29])[CH:11]=2)=[O:7])[CH3:4]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 59264773HCID 59264773, compound

Product 1

HCID 59264719HCID 59264719, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Iodomethane (0.10 ml, 12 equiv.) was added to a solution of 6-Ethyl-3-(4-fluoro-phenyl)-7-hydroxy-4-oxo-4H-chromene-2-carboxylic acid ethyl ester (50 mg, 0.14 mmol) and potassium carbonate (58 mg, 3.0 equiv.) in acetone and the mixture refluxed overnight. The volatiles were then evaporated in vacuo and the residue partitioned between water (15 ml) and EtOAc (15 ml). The organic layer was washed with brine, dried over MgSO4 and evaporated to dryness in vacuo to give a white crystalline product (45 mg, 87% yield)

Workup

  1. temperaturethe mixture refluxed overnight
  2. customThe volatiles were then evaporated in vacuo
  3. customthe residue partitioned between water (15 ml) and EtOAc (15 ml)
  4. washThe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-e21deee69c55410bbd7ed2c680ab5dba
Source dataset
uspto-grants-2010_04
Patent number
US07705027B2

Reaction notes

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