Methyl morpholine oxide → 2-Chloro-5-phenyl-1-(phenylsulfonyl)-1H-pyrrole-3-carbaldehyde

HRID 554309Notes

Reaction equation

HRID 554309 reaction equation
[Cl:1][C:2]1[N:3]([S:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)(=[O:17])=[O:16])[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:5][C:6]=1[CH2:7][OH:8].C[N+]1([O-])CCOCC1>C(#N)C.C(OCC)(=O)C.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[Cl:1][C:2]1[N:3]([S:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)(=[O:17])=[O:16])[C:4]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)=[CH:5][C:6]=1[CH:7]=[O:8]

Participants

6

Reactant 2

HCID 82029Methyl morpholine oxideHCID 66924752[2-Chloro-5-phenyl-1-(phenylsulfonyl)-1H-pyrrol-3-yl]methanol

Product 1

HCID 862328822-Chloro-5-phenyl-1-(phenylsulfonyl)-1H-pyrrole-3-carbaldehydeYield 53.3%

Reagents, catalysts & solvents 3

HCID 178419074HCID 178419074, compoundCatalystHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution (50 mL) of [2-chloro-5-phenyl-1-(phenylsulfonyl)-1H-pyrrol-3-yl]methanol (830 mg) in acetonitrile were added tetra-n-propylammonium perruthenate (84 mg), N-methylmorpholine N-oxide (484 mg) and molecular sieves 4A powder (2.0 g), and the mixture was stirred at room temperature for 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=19:1→4:1) to give the title compound as a colorless oil (yield 440 mg, 53%).

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=19:1→4:1)

Sources & evidence

ORD record
ord-d63e79f391b849ca92a511809fed5ad9
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Reaction notes

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