Dimethyl Sulfoxide → 2-Methyl-1-(phenylsulfonyl)-1H-pyrrole-3-carbaldehyde

HRID 554298Notes

Reaction equation

HRID 554298 reaction equation
[CH3:1][C:2]1[N:3]([S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)(=[O:11])=[O:10])[CH:4]=[CH:5][C:6]=1[CH2:7][OH:8].CS(C)=O.S(=O)(=O)=O.C(=O)([O-])O.[Na+]>C(N(CC)CC)C>[CH3:1][C:2]1[N:3]([S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)(=[O:10])=[O:11])[CH:4]=[CH:5][C:6]=1[CH:7]=[O:8]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 24682Sulfur trioxideHCID 516892Sodium BicarbonateHCID 66924976[2-methyl-1-(phenylsulfonyl)-1H-pyrrol-3-yl]methanol

Product 1

HCID 862328242-Methyl-1-(phenylsulfonyl)-1H-pyrrole-3-carbaldehydeYield 84%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a mixture of [2-methyl-1-(phenylsulfonyl)-1H-pyrrol-3-yl]methanol (6.35 g), dimethyl sulfoxide (50 mL) and triethylamine (25 mL) was added sulfur trioxide.pyridine complex (4.57 g), and the mixture was stirred at room temperature for 12 hr. Saturated aqueous sodium hydrogencarbonate solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogencarbonate solution, water and saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=2:1) to give a white title compound (yield 5.27 g, 84%).

Workup

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

Sources & evidence

ORD record
ord-2cf5c4c266ec4493bc24afb9aa3310e6
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Reaction notes

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