Methyl iodide → HCID 59264719, compound

HRID 2097318Notes

Reaction equation

HRID 2097318 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-78ed7c636a9145b8bee16f4171e4f8f0
Source dataset
uspto-grants-2013_05
Patent number
US08450310B2

Reaction notes

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