Methyl morpholine oxide → HCID 86232905, compound

HRID 554164Notes

Reaction equation

HRID 554164 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:14][C:13]([CH2:22][OH:23])=[CH:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C[N+]1([O-])CCOCC1>C(#N)C.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]2[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:14][C:13]([CH:22]=[O:23])=[CH:12]2)(=[O:10])=[O:9])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 66924646HCID 66924646, compound

Product 1

HCID 86232905HCID 86232905, compoundYield 82.5%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

To a solution (10 mL) of {1-[(4-methylphenyl)sulfonyl]-5-phenyl-1H-pyrrol-3-yl}methanol (1.50 g) in acetonitrile were added tetra-n-propylammonium perruthenate (150 mg), N-methylmorpholine N-oxide (932 mg) and molecular sieves 4A powder (1.5 g), and the mixture was stirred at room temperature for 1 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=6:1→1:1) to give the title compound as a brown oil (yield 1.23 g, 82%).

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=6:1→1:1)

Sources & evidence

ORD record
ord-8135cf02f2b14a49afff0ef8a2754d80
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Reaction notes

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