Methyl morpholine oxide → 5-(4-Bromo-phenyl)-3-methyl-isoxazole-4-carbaldehyde

HRID 1624374Notes

Reaction equation

HRID 1624374 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[C:10]([CH3:13])[C:9]=2[CH2:14][OH:15])=[CH:4][CH:3]=1.C[N+]1([O-])CCOCC1>C(Cl)Cl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:12][N:11]=[C:10]([CH3:13])[C:9]=2[CH:14]=[O:15])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 58218538[5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-yl]-methanol

Product 1

HCID 821337925-(4-Bromo-phenyl)-3-methyl-isoxazole-4-carbaldehyde

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

[5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-yl]-methanol (1.2 g, 4.5 mmol) was treated with 4-methylmorpholine N-oxide (0.786 g, 6.7 mmol) and tetrapropylammonium perruthenate (catalytic) in CH2Cl2. The reaction was monitored by analytical LCMS and when complete it was filtered through Celite then submitted to silica gel chromatography to give the title compound.

Workup

  1. filtrationwas filtered through Celite

Sources & evidence

ORD record
ord-6bb49464bf4945c6bb222deef50dc9ee
Source dataset
uspto-grants-2014_07
Patent number
US08778983B2

Reaction notes

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