Water → Methyl {6-[(4-ethoxybenzyl)oxy]-1-benzofuran-3-yl}acetate

HRID 1888706Notes

Reaction equation

HRID 1888706 reaction equation
[OH:1][C:2]1[CH:15]=[CH:14][C:5]2[C:6]([CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:7][O:8][C:4]=2[CH:3]=1.Cl[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH3:26])=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH2:25]([O:24][C:21]1[CH:22]=[CH:23][C:18]([CH2:17][O:1][C:2]2[CH:15]=[CH:14][C:5]3[C:6]([CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:7][O:8][C:4]=3[CH:3]=2)=[CH:19][CH:20]=1)[CH3:26]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 20639711-(Chloromethyl)-4-EthoxybenzeneHCID 20770861Methyl 2-(6-hydroxy-1-benzofuran-3-yl)acetate

Product 1

HCID 58047549Methyl {6-[(4-ethoxybenzyl)oxy]-1-benzofuran-3-yl}acetateYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl (6-hydroxy-1-benzofuran-3-yl)acetate (10.0 g, 48.5 mmol) in DMF (100 mL) were added 1-(chloromethyl)-4-ethoxybenzene (12.4 g, 72.7 mmol) and potassium carbonate (13.5 g, 97.0 mmol), and the mixture was stirred at room temperature for 3 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed twice with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was washed with diethyl ether and hexane to give the title compound (15.8 g, yield 96%) as a white solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed twice with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. washthe residue was washed with diethyl ether and hexane

Sources & evidence

ORD record
ord-4265bbe240764c999ee95da68580826f
Source dataset
uspto-grants-2013_08
Patent number
US08501804B2

Reaction notes

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