Potassium Carbonate → Methyl (3-(2-hydroxyethyl)benzofuran-7-yloxy)acetate

HRID 430748Notes

Reaction equation

HRID 430748 reaction equation
[OH:1][C:2]1[C:10]2[O:9][CH:8]=[C:7]([CH2:11][CH2:12][OH:13])[C:6]=2[CH:5]=[CH:4][CH:3]=1.Br[CH2:15][C:16]([O:18][CH3:19])=[O:17].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[OH:13][CH2:12][CH2:11][C:7]1[C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([O:1][CH2:15][C:16]([O:18][CH3:19])=[O:17])[C:10]=2[O:9][CH:8]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 111596397-Hydroxy-3-(2-hydroxyethyl)benzofuran

Product 1

HCID 11230436Methyl (3-(2-hydroxyethyl)benzofuran-7-yloxy)acetateYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

7-hydroxy-3-(2-hydroxyethyl)benzofuran (1.09 g), methyl bromoacetate (0.86 ml) and potassium carbonate (930 mg) were added to DMF (50 ml) and the mixture was stirred at room temperature for 18 hours. After filtering the reaction solution, the filtrate was concentrated and added to water layer (150 ml), followed by extracting the resultant twice with ethyl acetate (20 ml). After combining the organic layers, the resultant was washed with saturated brine and dried over sodium sulfate. After removing the sodium sulfate by filtration, the solvent was removed under reduced pressure and the residue was purified by column chromatography (solvent: hexane/ethyl acetate=1/1) using silica gel to obtain the desired compound (1.48 g, yield: 97%).

Workup

  1. filtrationAfter filtering the reaction solution
  2. concentrationthe filtrate was concentrated
  3. additionadded to water layer (150 ml)
  4. extractionby extracting the resultant twice with ethyl acetate (20 ml)
  5. washthe resultant was washed with saturated brine
  6. dry with materialdried over sodium sulfate
  7. customAfter removing the sodium sulfate
  8. filtrationby filtration
  9. customthe solvent was removed under reduced pressure
  10. customthe residue was purified by column chromatography (solvent: hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-d42a97a0e81c45a5a597ed71a8901a06
Source dataset
uspto-grants-2001_11
Patent number
US06323235B1

Reaction notes

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