Potassium Carbonate → HCID 20708444, compound

HRID 430797Notes

Reaction equation

HRID 430797 reaction equation
C([O:4][CH:5]([CH2:20][CH2:21][CH:22]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:6][C:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[C:15]([O:16]C(=O)C)[C:10]=2[O:9][CH:8]=1)(=O)C.[OH-].[Na+].C(=O)([O-])[O-].[K+].[K+].Br[CH2:44][C:45]([O:47][CH3:48])=[O:46].[Cl-].[NH4+]>CO.CN(C=O)C>[OH:4][CH:5]([CH2:20][CH2:21][CH:22]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[CH2:6][C:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[C:15]([O:16][CH2:44][C:45]([O:47][CH3:48])=[O:46])[C:10]=2[O:9][CH:8]=1

Participants

8

Reactant 5

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 60984Methyl bromoacetateHCID 18351834HCID 18351834, compound

Product 1

HCID 20708444HCID 20708444, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

3-(2-acetoxy-5, 5-diphenylpentyl)-7-acetoxybenzofuran (184 mg) was dissolved in methanol (5 ml) and the obtained solution was stirred at room temperature. To this solution, 1N aqueous sodium hydroxide solution (1 ml) was added and the resulting solution was stirred at room temperature. After confirming vanishment of the materials, the solvent was removed under reduced pressure. Water (5 ml) was added to the obtained residue and the resultant was extracted three times with ethyl acetate (10 ml). The organic layers were combined and washed with saturated brine, followed by drying over sodium sulfate. The sodium sulfate was removed by filtration and the solvent was removed under reduced pressure to obtain a crude product. The obtained crude product was dissolved in DMF (3 ml) and the obtained solution was stirred at room temperature. To this solution, potassium carbonate (100 mg) and methyl bromoacetate (0.10 ml) were added and the resultant was stirred at room temperature. After confirming vanishment of the materials, the reaction solution was poured into saturated aqueous ammonium chloride solution and extracted three times with ethyl acetate (10 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=3/1-2/1) using silica gel to obtain the desired compound (184 mg, yield: 100%).

Workup

  1. stirringthe resulting solution was stirred at room temperature
  2. customthe solvent was removed under reduced pressure
  3. additionWater (5 ml) was added to the obtained residue
  4. extractionthe resultant was extracted three times with ethyl acetate (10 ml)
  5. washwashed with saturated brine
  6. dry with materialby drying over sodium sulfate
  7. customThe sodium sulfate was removed by filtration
  8. customthe solvent was removed under reduced pressure
  9. customto obtain a crude product
  10. customThe obtained crude product
  11. stirringthe obtained solution was stirred at room temperature
  12. stirringthe resultant was stirred at room temperature
  13. extractionextracted three times with ethyl acetate (10 ml)
  14. washwashed with saturated brine
  15. dry with materialby drying over sodium sulfate
  16. customAfter removing the sodium sulfate
  17. filtrationby filtration
  18. customthe solvent was removed under reduced pressure
  19. customthe residue was purified by column chromatography (solvent: hexane/ethyl acetate=3/1-2/1)

Sources & evidence

ORD record
ord-170fe8f01bdd4f78b5dc2c0483703ef3
Source dataset
uspto-grants-2001_11
Patent number
US06323235B1

Reaction notes

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