Water → HCID 10892558, compound

HRID 430005Notes

Reaction equation

HRID 430005 reaction equation
[C:1]1([S:7]([O:10][C:11]2[CH:16]=[CH:15][C:14]([S:17][CH2:18][C:19]#[CH:20])=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.O.C1(C)C=CC(S(O)(=O)=[O:30])=CC=1>COCCOC>[C:1]1([S:7]([O:10][C:11]2[CH:12]=[CH:13][C:14]3[S:17][CH:18]=[C:19]([CH2:20][OH:30])[C:15]=3[CH:16]=2)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 521998p-Toluenesulfonic acid monohydrateHCID 10924734HCID 10924734, compound2×

Product 1

HCID 10892558HCID 10892558, compoundYield 187.8%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

The compound (3) (65.47 g, 183 mmol) obtained in above (2) was dissolved in 1,2-dimethoxyethane (1.6L) and the solution was refluxed for 4 hours. To the solution were added water (64 ml) and p-toluenesulfonic acid monohydrate (19.2 g, 100 mmol) and refluxing was continued for 2 hours. The reaction mixture was concentrated under reduced pressure. After water (200 ml) was added to the resulting oil, the mixture was extracted with ethyl acetate (300 ml). The organic layer was washed with aqueous sodium hydrogen carbonate and water, dried over anhydrous magnesium sulfate and then the solvent was distilled off under reduced pressure to provide 60.18 g of the title compound (4) as oil. Crude yield: 103%.

Workup

  1. temperaturethe solution was refluxed for 4 hours
  2. temperaturerefluxing
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionAfter water (200 ml) was added to the resulting oil
  5. extractionthe mixture was extracted with ethyl acetate (300 ml)
  6. washThe organic layer was washed with aqueous sodium hydrogen carbonate and water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-d27b620dbe844f5e9ac5a9a1249e15b8
Source dataset
uspto-grants-2001_11
Patent number
US06320060B1

Reaction notes

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