Acetic Acid → HCID 18351579, compound

HRID 430761Notes

Reaction equation

HRID 430761 reaction equation
[H-].[Na+].[CH:3]([C:5]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[C:6]=1[O:7][CH:8]([CH3:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:4].C(O)(=O)C>CN(C=O)C>[CH3:20][O:19][C:15]1[C:6]2[O:7][C:8]([CH3:14])([C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:3](=[O:4])[C:5]=2[CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24758Sodium hydrideHCID 18351607HCID 18351607, compound

Product 1

HCID 18351579HCID 18351579, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Sodium hydride (60% dispersion in oil, 6.61 g) was added to DMF (250 ml). To this solution, a solution of ethyl 2-(2-formyl-6-methoxyphenoxy)-propionate (34.56 g) in DMF (150 ml) was added dropwise at room temperature for 1 hour, and the resulting solution was stirred for another 30 minutes. Acetic acid (12 ml) was added to the reaction solution and the solution was concentrated. The solution was poured into water layer (300 ml) and the resultant was extracted twice with ethyl acetate (150 ml). The organic layers were combined and washed with saturated brine, followed by drying over sodium sulfate. After removing sodium sulfate by filtration, the solvent was removed under reduced pressure and the obtained residue was dissolved in dichloromethane (600 ml). To this solution, Celite (105 g) and pyridinium chlorochromate (44.52 g) were added and the solution was stirred at room temperature for 21 hours. Isopropyl alcohol (20 ml) was added to the reaction solution and the resulting solution was stirred for 15 minutes. One liter of hexane was added to the reaction solution and the resultant was filtered through Celite, followed by washing the precipitate with one liter of ether. The filtrate was washed with water (500 ml) and the aqueous layer was extracted with ether (200 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=5/1-3/1) using silica gel to obtain the desired compound (20.39 g, yield: 60%).

Workup

  1. concentrationthe solution was concentrated
  2. additionThe solution was poured into water layer (300 ml)
  3. extractionthe resultant was extracted twice with ethyl acetate (150 ml)
  4. washwashed with saturated brine
  5. dry with materialby drying over sodium sulfate
  6. customAfter removing sodium sulfate
  7. filtrationby filtration
  8. customthe solvent was removed under reduced pressure
  9. dissolutionthe obtained residue was dissolved in dichloromethane (600 ml)
  10. additionTo this solution, Celite (105 g) and pyridinium chlorochromate (44.52 g) were added
  11. stirringthe solution was stirred at room temperature for 21 hours
  12. additionIsopropyl alcohol (20 ml) was added to the reaction solution
  13. stirringthe resulting solution was stirred for 15 minutes
  14. additionOne liter of hexane was added to the reaction solution
  15. filtrationthe resultant was filtered through Celite
  16. washby washing the precipitate with one liter of ether
  17. washThe filtrate was washed with water (500 ml)
  18. extractionthe aqueous layer was extracted with ether (200 ml)
  19. washwashed with saturated brine
  20. dry with materialby drying over sodium sulfate
  21. customAfter removing the sodium sulfate
  22. filtrationby filtration
  23. customthe solvent was removed under reduced pressure
  24. customthe residue was purified by column chromatography (solvent: hexane/ethyl acetate=5/1-3/1)

Sources & evidence

ORD record
ord-7b4d687b01f5440bbcb64ca0199df281
Source dataset
uspto-grants-2001_11
Patent number
US06323235B1

Reaction notes

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