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

HRID 1183267Notes

Reaction equation

HRID 1183267 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-f93e1b73f3db4e78b7204b52935873f6
Source dataset
uspto-grants-2014_03
Patent number
US08664220B2

Reaction notes

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