Water → HCID 53707420, compound

HRID 430796Notes

Reaction equation

HRID 430796 reaction equation
[C:1]([O:4][CH2:5][CH2:6][CH2:7][C:8]1[O:9][C:10]2[C:19]([O:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])=[CH:18][CH:17]=[CH:16][C:11]=2[C:12]=1[CH2:13][CH2:14]O)(=[O:3])[CH3:2].C(N([CH2:31][CH3:32])CC)C.[CH3:33][S:34](Cl)(=O)=O.O>ClCCl>[C:1]([O:4][CH2:5][CH2:6][CH2:7][C:8]1[O:9][C:10]2[C:19]([O:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])=[CH:18][CH:17]=[CH:16][C:11]=2[C:12]=1[CH2:13][CH2:14][S:34][CH:33]([C:32]1[CH:31]=[CH:8][CH:7]=[CH:6][CH:5]=1)[C:10]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:11]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 11187199HCID 11187199, compound

Product 1

HCID 53707420HCID 53707420, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Methyl (2-(3-acetoxypropyl)-3-(2-hydroxyethyl)benzofuran-7-yloxy)acetate (78 mg) was dissolved in dichloromethane (1 ml) and the obtained solution was cooled to 0° C. To this solution, triethylamine (0.02 ml) and methanesulfonyl chloride (0.047 ml) were added and the resulting mixture was stirred for 30 minutes. The reaction solution was poured into water (50 ml) and 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 over sodium sulfate. After removing the sodium sulfate by filtration, the solvent was removed under reduced pressure and the obtained residue was dissolved in DMF (2 ml). To this solution, diphenylmethanethiol (89 mg) and potassium carbonate (37 mg) were added and the resultant was stirred at room temperature for 22 hours. The reaction mixture 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 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 (83 mg, yield: 70%).

Workup

  1. extractionextracted twice with ethyl acetate (20 ml)
  2. washwashed with saturated aqueous sodium hydrogen carbonate solution and with saturated brine
  3. dry with materialby drying over sodium sulfate
  4. customAfter removing the sodium sulfate
  5. filtrationby filtration
  6. customthe solvent was removed under reduced pressure
  7. dissolutionthe obtained residue was dissolved in DMF (2 ml)
  8. additionTo this solution, diphenylmethanethiol (89 mg) and potassium carbonate (37 mg) were added
  9. stirringthe resultant was stirred at room temperature for 22 hours
  10. additionThe reaction mixture was poured into water (50 ml)
  11. extractionthe resultant was extracted twice with ethyl acetate (20 ml)
  12. washwashed with saturated aqueous sodium hydrogen carbonate solution and 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=2/1)

Sources & evidence

ORD record
ord-b12d3c9d9cd24aa78ebbaf5ac6e07fce
Source dataset
uspto-grants-2001_11
Patent number
US06323235B1

Reaction notes

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