Methyl morpholine oxide → HCID 86620747, compound

HRID 554311Notes

Reaction equation

HRID 554311 reaction equation
[Cl:1][C:2]1[N:3]([S:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)(=[O:18])=[O:17])[C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:5]([F:9])[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:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)(=[O:18])=[O:17])[C:4]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[C:5]([F:9])[C:6]=1[CH:7]=[O:8]

Participants

6

Reactant 2

HCID 82029Methyl morpholine oxideHCID 66924737HCID 66924737, compound

Product 1

HCID 86620747HCID 86620747, compoundYield 67%

Reagents, catalysts & solvents 3

HCID 178419074HCID 178419074, compoundCatalystHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution (15 mL) of [2-chloro-4-fluoro-5-phenyl-1-(phenylsulfonyl)-1H-pyrrol-3-yl]methanol (210 mg) in acetonitrile were added tetra-n-propylammonium perruthenate (31 mg), N-methylmorpholine N-oxide (156 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=90:10→85:15) to give the title compound as a colorless oil (yield 140 mg, 67%).

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=90:10→85:15)

Sources & evidence

ORD record
ord-792cf70a5a3844a3ae6f6337a13c0ea0
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Reaction notes

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