Potassium Carbonate → HCID 53884645, compound

HRID 843162Notes

Reaction equation

HRID 843162 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].C(=O)([O-])[O-].[K+].[K+].I[CH2:24][CH2:25][OH:26]>C(#N)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][CH2:24][CH2:25][OH:26])[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12225IodoethanolHCID 748649Ethyl 4-hydroxy-3-methyl-1-benzofuran-2-carboxylate

Product 1

HCID 53884645HCID 53884645, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-Hydroxy-3-methyl-benzofuran-2-carboxylic acid ethyl ester (100 mg), potassium carbonate (500 mg) and 2-iodoethanol (195 μl) were suspended in acetonitrile (10 ml). The mixture was refluxed overnight. Inorganic salt was filtered out and the mother solution was evaporated to dryness. The residue was dissolved in ethyl acetate, washed with water, dried over anhydrous sodium sulfate and evaporated to dryness. The residue was purified by silica gel column chromatography developed by ethyl acetate-hexane to give 4-(2-hydroxy-ethoxy)-3-methyl-benzofuran-2-carboxylic acid ethyl ester (77 mg) as a white powder. FAB-MS: m/z 265 (MH+).

Workup

  1. temperatureThe mixture was refluxed overnight
  2. filtrationInorganic salt was filtered out
  3. customthe mother solution was evaporated to dryness
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated to dryness
  8. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-88bf37ba927141a7a7d03672226c701b
Source dataset
uspto-grants-2002_04
Patent number
US06376491B1

Reaction notes

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