Tetrahydrofuran → 3-methyl-5-[(4-methylphenyl)sulfonyl]-4-phenyl-1H-pyrrole-2-carbaldehyde

HRID 2359937Notes

Reaction equation

HRID 2359937 reaction equation
[CH3:1][C:2]1[C:3]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:4]([S:7]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)(=[O:9])=[O:8])[NH:5][CH:6]=1.[Cl-].ClC=[N+](C)C.[O:29]1CCC[CH2:30]1.C(=O)([O-])O.[Na+]>C(#N)C>[CH3:1][C:2]1[C:3]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:4]([S:7]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)(=[O:8])=[O:9])[NH:5][C:6]=1[CH:30]=[O:29]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 77311Chloro-N,N-dimethylformiminium chlorideHCID 516892Sodium BicarbonateHCID 21860915HCID 21860915, compound

Product 1

HCID 236608463-methyl-5-[(4-methylphenyl)sulfonyl]-4-phenyl-1H-pyrrole-2-carbaldehydeYield 46%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-Methyl-2-[(4-methylphenyl)sulfonyl]-3-phenyl-1H-pyrrole (374 mg) and (chloromethylene)dimethylammonium chloride (872 mg) were stirred at 60° C. for 16 hr in a mixed solvent of tetrahydrofuran (10 mL) and acetonitrile (5 mL). The reaction mixture was cooled to room temperature, saturated aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine in this order, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=4:1) to give the title compound as a pale-yellow solid (yield 187 mg, 46%).

Workup

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

Sources & evidence

ORD record
ord-b8e8f8399ef944a188b16f9c141c2da2
Source dataset
uspto-grants-2014_04
Patent number
US08686010B2

Reaction notes

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