Water → HCID 11473142, compound

HRID 430753Notes

Reaction equation

HRID 430753 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[O:5][C:6]2[C:21]([O:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])=[CH:20][CH:19]=[CH:18][C:7]=2[C:8]=1[CH2:9][CH2:10][O:11]C1CCCCO1.N1C=CC=CC=1.[C:34](OC(=O)C)(=[O:36])[CH3:35].O>C1COCC1>[C:34]([O:1][CH2:2][CH2:3][C:4]1[O:5][C:6]2[C:21]([O:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])=[CH:20][CH:19]=[CH:18][C:7]=2[C:8]=1[CH2:9][CH2:10][OH:11])(=[O:36])[CH3:35]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 11451751HCID 11451751, compound

Product 1

HCID 11473142HCID 11473142, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl (2-(2-hydroxyethyl)-3-(2-tetrahydropyranyloxyethyl)benzofuran-7-yloxy)acetate (403 mg), pyridine (0.13 ml) and acetic anhydride (0.3 ml) were dissolved in THF (5 ml) and the solution was stirred at room temperature for 16 hours. The reaction solution was poured into water (50 ml) and the organic layer was separated, followed by extraction twice with ethyl acetate (20 ml). The organic layers were combined and washed with 1N hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and with saturated brine, followed by drying the resultant over sodium sulfate. After removing sodium sulfate by filtration, the solvent was removed under reduced pressure and the residue was dissolved in methanol (4 ml). To this solution, 1N hydrochloric acid (1 ml) was added and the solution was stirred at room temperature for 2 hours. The reaction solution was poured into water (50 ml) and the resultant was extracted twice with ethyl acetate (20 ml). The organic layers were combined and washed with saturated aqueous sodium hydrogen carbonate solution and with saturated brine, followed by drying the resultant 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=1/2) using silica gel to obtain the desired compound (412 mg, yield: 42%).

Workup

  1. customthe organic layer was separated
  2. extractionfollowed by extraction twice with ethyl acetate (20 ml)
  3. washwashed with 1N hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and with saturated brine
  4. dry with materialby drying the resultant over sodium sulfate
  5. customAfter removing sodium sulfate
  6. filtrationby filtration
  7. customthe solvent was removed under reduced pressure
  8. dissolutionthe residue was dissolved in methanol (4 ml)
  9. additionTo this solution, 1N hydrochloric acid (1 ml) was added
  10. stirringthe solution was stirred at room temperature for 2 hours
  11. additionThe reaction solution was poured into water (50 ml)
  12. extractionthe resultant was extracted twice with ethyl acetate (20 ml)
  13. washwashed with saturated aqueous sodium hydrogen carbonate solution and with saturated brine
  14. dry with materialby drying the resultant over sodium sulfate
  15. customAfter removing the sodium sulfate
  16. filtrationby filtration
  17. customthe solvent was removed under reduced pressure
  18. customthe residue was purified by column chromatography (solvent: hexane/ethyl acetate=1/2)

Sources & evidence

ORD record
ord-841dfe15595449c794f5ede62bbbeced
Source dataset
uspto-grants-2001_11
Patent number
US06323235B1

Reaction notes

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