Methyl iodide → HCID 68716639, compound

HRID 29424Notes

Reaction equation

HRID 29424 reaction equation
[C:1]([O:5][C:6]([C:8]1[O:9][C:10]2[CH:17]=[CH:16][C:15]([CH3:18])=[C:14]([OH:19])[C:11]=2[C:12]=1[CH3:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].IC.[C:22]([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[C:1]([O:5][C:6]([C:8]1[O:9][C:10]2[CH:17]=[CH:16][C:15]([CH3:18])=[C:14]([O:19][CH3:22])[C:11]=2[C:12]=1[CH3:13])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 68707780HCID 68707780, compound

Product 1

HCID 68716639HCID 68716639, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 80 mg of 4-hydroxy-3,5-dimethyl-benzofuran-2-carboxylic acid tert-butyl ester was added 1 mL of iodomethane, 80 mg of K2CO3 and 1 mL of DMF. The mixture was stirred at room temperature overnight. The reaction mixture was washed with brine and extracted with ethyl acetate. The combined ethyl acetate solution was washed with brine. Removal of the solvent gave 82 mg of 4-methoxy-3,5-dimethyl-benzofuran-2-carboxylic acid tert-butyl ester as a pale yellow solid.

Workup

  1. washThe reaction mixture was washed with brine
  2. extractionextracted with ethyl acetate
  3. washThe combined ethyl acetate solution was washed with brine
  4. customRemoval of the solvent

Sources & evidence

ORD record
ord-03cc3561d1534fcab575109e3b194a44
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

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