Water → HCID 53638626, compound

HRID 430755Notes

Reaction equation

HRID 430755 reaction equation
[CH:1]([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][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][O:13]1)=[CH:2][CH3:3].[CH2:28]1[C:33](=[O:34])N(Br)C(=O)C1.[OH2:36]>C1C=CC=CC=1>[C:33]([O:34][CH2:3][CH:2]=[CH:1][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][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][O:13]1)(=[O:36])[CH3:28]

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 54506684HCID 54506684, compound

Product 1

HCID 53638626HCID 53638626, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Methyl (2-(1-propenyl)-3-(2-tetrahydropyranyloxyethyl)benzofuran-7-yloxy)acetate (523 mg) was dissolved in benzene (5 ml) and NBS (299 mg) and azoisobutylonitrile (23 mg) were added, followed by stirring the mixture for 4 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 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 DMF (4 ml). Potassium acetate (205 mg) was added to this solution and the solution was stirred at room temperature for 50 minutes. The reaction solution was added to water (50 ml) and the resultant was extracted twice with ethyl acetate (20 ml). The organic layers were combined and washed with saturated brine and dried 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=2/1) using silica gel to obtain the desired compound (217 mg, yield: 36%).

Workup

  1. extractionthe resultant was extracted twice with ethyl acetate (20 ml)
  2. washwashed with saturated brine
  3. dry with materialby drying the resultant over sodium sulfate
  4. customAfter removing sodium sulfate
  5. filtrationby filtration
  6. customthe solvent was removed under reduced pressure
  7. dissolutionthe residue was dissolved in DMF (4 ml)
  8. additionPotassium acetate (205 mg) was added to this solution
  9. stirringthe solution was stirred at room temperature for 50 minutes
  10. additionThe reaction solution was added to water (50 ml)
  11. extractionthe resultant was extracted twice with ethyl acetate (20 ml)
  12. washwashed with saturated brine
  13. dry with materialdried 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=2/1)

Sources & evidence

ORD record
ord-ba6b654a0bba49ea891fe9040f113532
Source dataset
uspto-grants-2001_11
Patent number
US06323235B1

Reaction notes

Loading…