Water → HCID 18351724, compound

HRID 430768Notes

Reaction equation

HRID 430768 reaction equation
[CH3:1][O:2][C:3]1[C:11]2[O:10][CH:9]=[C:8]([C:12](O)=O)[C:7]=2[CH:6]=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:21](Br)[C:22]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=O.O.C[N:33]([CH:35]=[O:36])C>>[C:24]1([C:22]2[N:33]=[C:35]([CH2:12][C:8]3[C:7]4[CH:6]=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[C:11]=4[O:10][CH:9]=3)[O:36][CH:21]=2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 6259Phenacyl bromideHCID 11430Potassium CarbonateHCID 128446037-methoxy-1-benzofuran-3-carboxylic acid

Product 1

HCID 18351724HCID 18351724, compoundYield 47%

Procedure

7-methoxy-benzofuran-3-carboxylic acid (294 mg) was dissolved in DMF (5 ml). To this solution, potassium carbonate (237 mg) and phenacyl bromide (342 mg) were added, and the resulting solution was stirred at room temperature for 30 minutes. The reaction mixture was poured into water layer (50 ml) and extracted twice with ethyl acetate (20 ml). The organic layers were combined and washed with saturated brine, followed by drying over sodium sulfate. Sodium sulfate was removed by filtration and the solvent was removed under reduced pressure. The residue was dissolved in acetic acid (5 ml) and ammonium acetate (551 mg) was added, followed by refluxing the resulting solution for 4 hours. After cooling the reaction solution to room temperature, the solution was poured into water layer (100 ml) and extracted twice with ethyl acetate (30 ml). The organic layers were combined and washed with saturated brine, followed by drying 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=5/1) using silica gel to obtain the desired compound (203 mg, yield: 47%).

Workup

  1. extractionextracted twice with ethyl acetate (20 ml)
  2. washwashed with saturated brine
  3. dry with materialby drying over sodium sulfate
  4. customSodium sulfate was removed by filtration
  5. customthe solvent was removed under reduced pressure
  6. dissolutionThe residue was dissolved in acetic acid (5 ml)
  7. additionammonium acetate (551 mg) was added
  8. temperatureby refluxing the resulting solution for 4 hours
  9. temperatureAfter cooling the reaction solution to room temperature
  10. additionthe solution was poured into water layer (100 ml)
  11. extractionextracted twice with ethyl acetate (30 ml)
  12. washwashed with saturated brine
  13. dry with materialby drying over sodium sulfate
  14. customAfter removing the sodium sulfate
  15. filtrationby filtration
  16. customthe solvent was removed under reduced pressure
  17. customthe residue was purified by column chromatography (solvent: hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-9f3bc072c7074d9288fb39247d3c3d11
Source dataset
uspto-grants-2001_11
Patent number
US06323235B1

Reaction notes

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