Methyl morpholine oxide → 5-Phenyl-1-(2-thienylsulfonyl)-1H-pyrrole-3-carbaldehyde

HRID 554303Notes

Reaction equation

HRID 554303 reaction equation
[C:1]1([C:7]2[N:11]([S:12]([C:15]3[S:16][CH:17]=[CH:18][CH:19]=3)(=[O:14])=[O:13])[CH:10]=[C:9]([CH2:20][OH:21])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[N+]1([O-])CCOCC1>C(#N)C.C(OCC)(=O)C.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[C:1]1([C:7]2[N:11]([S:12]([C:15]3[S:16][CH:17]=[CH:18][CH:19]=3)(=[O:14])=[O:13])[CH:10]=[C:9]([CH:20]=[O:21])[CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 2

HCID 82029Methyl morpholine oxideHCID 66924716[5-Phenyl-1-(2-thienylsulfonyl)-1H-pyrrol-3-yl]methanol

Product 1

HCID 862328445-Phenyl-1-(2-thienylsulfonyl)-1H-pyrrole-3-carbaldehydeYield 57%

Reagents, catalysts & solvents 3

HCID 178419074HCID 178419074, compoundCatalystHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution (20 mL) of [5-phenyl-1-(2-thienylsulfonyl)-1H-pyrrol-3-yl]methanol (480 mg) in acetonitrile were added tetra-n-propylammonium perruthenate (80 mg), N-methylmorpholine N-oxide (407 mg) and molecular sieves 4A powder (500 mg), and the mixture was stirred at room temperature for 1.5 hr. The reaction mixture was diluted with ethyl acetate, filtered through celite, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=4:1→3:2) to give the title compound as colorless crystals (yield 272 mg, 57%).

Workup

  1. filtrationfiltered through celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=4:1→3:2)

Sources & evidence

ORD record
ord-14b2b850701c4e458a0291b2acc9eb75
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Reaction notes

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