Methyl iodide → Ethyl 3-methyl-4-methoxy-5-ethylbenzofuran-2-carboxylate

HRID 29319Notes

Reaction equation

HRID 29319 reaction equation
[CH3:1][C:2]1[C:6]2[C:7]([OH:13])=[C:8]([CH2:11][CH3:12])[CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15].[C:19](=O)([O-])[O-].[K+].[K+].IC>CN(C=O)C.CCOCC.O>[CH3:1][C:2]1[C:6]2[C:7]([O:13][CH3:19])=[C:8]([CH2:11][CH3:12])[CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 68711669Ethyl 3-methyl-4-hydroxy-5-ethylbenzofuran-2-carboxylate

Product 1

HCID 68717425Ethyl 3-methyl-4-methoxy-5-ethylbenzofuran-2-carboxylateYield 90.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.25 g (1.01 mmol) of ethyl 3-methyl-4-hydroxy-5-ethylbenzofuran-2-carboxylate in 3.0 mL of DMF was added 0.417 g (3 eq) of potassium carbonate and 0.63 mL (10 eq) of iodomethane and the reaction was stirred at room temperature for 14 h. The reaction was then diluted with ether and water. The organic layer was washed with water, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was chromatographed on silica gel eluting with ethyl acetate/hexanes (1:10) to provide 0.24 g of ethyl 3-methyl -4-methoxy-5-ethylbenzofuran-2-carboxylate.

Workup

  1. washThe organic layer was washed with water
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed on silica gel eluting with ethyl acetate/hexanes (1:10)

Sources & evidence

ORD record
ord-22ef2b6df11a44b298c2976888846593
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

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