Dimethylformamide → Ethyl 4-methoxy-3-methyl-2-benzofurancarboxylate

HRID 29340Notes

Reaction equation

HRID 29340 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].IC.[C:19]([O-])([O-])=O.[K+].[K+].CN(C=O)C>[Cl-].[Na+].O>[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:19])[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 748649Ethyl 4-hydroxy-3-methyl-1-benzofuran-2-carboxylate

Product 1

HCID 9497663Ethyl 4-methoxy-3-methyl-2-benzofurancarboxylateYield 76.1%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

4-Hydroxy-3-methyl-benzofuran-2-carboxylic acid ethyl ester (200 mg) was mixed with iodomethane (0.5 mL), K2CO3 (200 mg) and 2 mL of DMF. The mixture was stirred at room temperature overnight. The mixture was mixed with brine and extracted with ethyl acetate, and the combined ethyl acetate layers were washed with brine. Removal of the solvent gave the crude product that was purified by column chromatographt to give 162 mg (76% yield) of 4-methoxy-3-methyl-benzofuran-2-carboxylic acid ethyl ester as amber colored oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washthe combined ethyl acetate layers were washed with brine
  3. customRemoval of the solvent
  4. customgave the crude product that
  5. customwas purified by column chromatographt

Sources & evidence

ORD record
ord-cc5d13bd328440058eb6608bd0696981
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

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