Iodoethane → 4-Ethoxy-3-methyl-benzofuran-2-carboxylic acid ethyl ester

HRID 29344Notes

Reaction equation

HRID 29344 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:12]([OH:16])[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2].[CH2:17](I)[CH3:18].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH2:17][CH3:18])[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 748649Ethyl 4-hydroxy-3-methyl-1-benzofuran-2-carboxylate

Product 1

HCID 687122294-Ethoxy-3-methyl-benzofuran-2-carboxylic acid ethyl esterYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Hydroxy-3-methyl-benzofuran-2-carboxylic acid ethyl ester (200 mg) was mixed with ethyl iodide (0.5 mL), K2CO3 (200 mg) and 2 mL of DMF. The mixture was stirred at room temperature overnight. The mixture was washed with brine and extracted with ethyl acetate. The combined ethyl acetate layers were washed with brine. Removal of the solvent under vacuum gave the crude product, which was purified by column chromatography to give 175 mg (77% yield) of 4-ethoxy-3-methyl-benzofuran-2-carboxylic acid ethyl ester as white solid.

Workup

  1. washThe mixture was washed with brine
  2. extractionextracted with ethyl acetate
  3. washThe combined ethyl acetate layers were washed with brine
  4. customRemoval of the solvent under vacuum
  5. customgave the crude product, which
  6. customwas purified by column chromatography

Sources & evidence

ORD record
ord-51573b178c954b40b9c923f866c5ba9f
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

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