Methyl iodide → HCID 59487515, compound

HRID 886715Notes

Reaction equation

HRID 886715 reaction equation
[OH:1][CH:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([CH:11]=[O:12])[C:5]=2[C:4](=[O:13])[O:3]1.[C:14](=O)([O-])[O-].[K+].[K+].IC>CN(C)C=O>[CH:2]([C:6]1[CH:7]=[CH:8][CH:9]=[C:10]([CH:11]=[O:12])[C:5]=1[C:4]([O:3][CH3:14])=[O:13])=[O:1]

Participants

5

Reactant 3

HCID 6328Methyl iodide2×HCID 11430Potassium CarbonateHCID 12746936HCID 12746936, compound

Product 1

HCID 59487515HCID 59487515, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-hydroxy-3-oxo-1,3-dihydro-2-benzofuran-4-carbaldehyde (720 mg) in anhydrous dimethylformamide (4 ml) was added potassium carbonate (613 mg). It was stirred for 30 minutes to give a thick white suspension. Iodomethane (0.4 ml) was added and stirred for 3 days. More methyl iodide (0.4 ml) was added and stirring continued for 24 hours. Most of the dimethylformamide was evaporated in vacuo. The pale yellow residue was partitioned between ethyl acetate (25 ml) and water (25 ml) and the organic phase was washed with aqueous lithium chloride (50 ml) and saturated brine (25 ml), dried over sodium sulphate and evaporated to give a pale yellow solid (645 mg).

Workup

  1. customto give a thick white suspension
  2. stirringstirred for 3 days
  3. stirringstirring
  4. waitcontinued for 24 hours
  5. customMost of the dimethylformamide was evaporated in vacuo
  6. customThe pale yellow residue was partitioned between ethyl acetate (25 ml) and water (25 ml)
  7. washthe organic phase was washed with aqueous lithium chloride (50 ml) and saturated brine (25 ml)
  8. dry with materialdried over sodium sulphate
  9. customevaporated

Sources & evidence

ORD record
ord-069fc82789544708bfdfed9bc6f73a62
Source dataset
uspto-grants-2012_08
Patent number
US08247377B2

Reaction notes

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