Methyl morpholine oxide → 5-(2,6-difluorophenyl)-1H-pyrrole-3-carbaldehyde

HRID 1012458Notes

Reaction equation

HRID 1012458 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[NH:13][CH:12]=[C:11]([CH2:14][OH:15])[CH:10]=1.C[N+]1([O-])CCOCC1>C(#N)C.C(OCC)(=O)C.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[NH:13][CH:12]=[C:11]([CH:14]=[O:15])[CH:10]=1

Participants

6

Reactant 2

HCID 82029Methyl morpholine oxideHCID 66974511[5-(2,6-difluorophenyl)-1H-pyrrol-3-yl]methanol

Product 1

HCID 866309715-(2,6-difluorophenyl)-1H-pyrrole-3-carbaldehydeYield 77%

Reagents, catalysts & solvents 3

HCID 178419074HCID 178419074, compoundCatalystHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution (26 mL) of [5-(2,6-difluorophenyl)-1H-pyrrol-3-yl]methanol (2.56 g) in acetonitrile were added tetra-n-propylammonium perruthenate (430 mg), N-methylmorpholine N-oxide (2.15 g) and molecular sieves 4A powder (5 g), and the mixture was stirred at room temperature for 2 hr. The reaction mixture was diluted with ethyl acetate (60 mL) and filtered through celite. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=1:1) to give the title compound as pale-red crystals (yield 1.94 g, 77%).

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=1:1)

Sources & evidence

ORD record
ord-fa48f0e662ca4df59166dd3ae9a28c8b
Source dataset
uspto-grants-2011_07
Patent number
US07977488B2

Reaction notes

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