Sodium Thiosulfate → 5-[2-(methylsulfonyl)phenyl]-1H-pyrrole-3-carbaldehyde

HRID 2090718Notes

Reaction equation

HRID 2090718 reaction equation
CS[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[NH:13][CH:12]=[C:11]([CH:14]=[O:15])[CH:10]=1.Cl[C:17]1C=CC=C(C(OO)=O)C=1.[S:27]([O-:31])([O-])(=[O:29])=S.[Na+].[Na+]>C(OCC)(=O)C>[CH3:17][S:27]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[NH:13][CH:12]=[C:11]([CH:14]=[O:15])[CH:10]=1)(=[O:31])=[O:29]

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 866309885-[2-(methylthio)phenyl]-1H-pyrrole-3-carbaldehyde

Product 1

HCID 866309915-[2-(methylsulfonyl)phenyl]-1H-pyrrole-3-carbaldehydeYield 78%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-[2-(methylthio)phenyl]-1H-pyrrole-3-carbaldehyde (100 mg) in ethyl acetate (5 mL) was added 3-chloroperbenzoic acid (318 mg) under ice-cooling. After stirring at room temperature for 3 hr, a saturated sodium thiosulfate aqueous solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=1:1→1:3) to give the title compound as pale-yellow crystals (yield 88.9 mg, 78%).

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=1:1→1:3)

Sources & evidence

ORD record
ord-2d6c6ce513e34bd18d3780459fe11780
Source dataset
uspto-grants-2013_05
Patent number
US08436187B2

Reaction notes

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