Methyl morpholine oxide → 5-(4-Fluorophenyl)-2-methyl-1-(phenylsulfonyl)-1H-pyrrole-3-carbaldehyde

HRID 554305Notes

Reaction equation

HRID 554305 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([S:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)(=[O:15])=[O:14])[C:11]([CH3:22])=[C:10]([CH2:23][OH:24])[CH:9]=2)=[CH:4][CH:3]=1.C[N+]1([O-])CCOCC1>C(#N)C.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]([S:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)(=[O:15])=[O:14])[C:11]([CH3:22])=[C:10]([CH:23]=[O:24])[CH:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 66924671[5-(4-Fluorophenyl)-2-methyl-1-(phenylsulfonyl)-1H-pyrrol-3-yl]methanol

Product 1

HCID 866207465-(4-Fluorophenyl)-2-methyl-1-(phenylsulfonyl)-1H-pyrrole-3-carbaldehydeYield 66.1%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

[5-(4-Fluorophenyl)-2-methyl-1-(phenylsulfonyl)-1H-pyrrol-3-yl]methanol (1.08 g) was dissolved in acetonitrile (20 mL), tetra-n-propylammonium perruthenate (100 mg), N-methylmorpholine N-oxide (0.52 g) and molecular sieves 4A powder (1.00 g) were added, and the mixture was stirred at room temperature for 2 hr. The reaction mixture was concentrated under reduced pressure, and the residue was suspended in ethyl acetate and filtered through celite. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=3:1) to give the title compound as colorless crystals (yield 0.71 g, 66%).

Workup

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

Sources & evidence

ORD record
ord-7d88b6ed72da4fbe8377ccaebfce55f4
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Reaction notes

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