Water → HCID 66924723, compound

HRID 554277Notes

Reaction equation

HRID 554277 reaction equation
[CH2:1]([C:5]1[NH:9][CH:8]=[C:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:6]=1)[CH2:2][CH2:3][CH3:4].[H-].[Na+].[C:17]1([S:23](Cl)(=[O:25])=[O:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O>O1CCCC1>[CH2:1]([C:5]1[N:9]([S:23]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)(=[O:25])=[O:24])[CH:8]=[C:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 66924704HCID 66924704, compound

Product 1

HCID 66924723HCID 66924723, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under an argon atmosphere, ethyl 5-butyl-1H-pyrrole-3-carboxylate (976 mg) was dissolved in tetrahydrofuran (50 mL), sodium hydride (60% in oil, 240 mg) was added and the mixture was stirred at room temperature for 30 min. Benzenesulfonyl chloride (0.77 mL) was added, and the mixture was stirred at room temperature for 1 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=19:1→8:2), and the obtained solid was washed with hexane to give the title compound as a colorless solid (yield 780 mg, 47%).

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=19:1→8:2)
  7. washthe obtained solid was washed with hexane

Sources & evidence

ORD record
ord-a10b37ba383341e79c1b0bc6915ac669
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Reaction notes

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