Methyl morpholine oxide → 4-(Pyridin-3-yl)benzaldehyde

HRID 1603063Notes

Reaction equation

HRID 1603063 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:12]=[CH:11][C:10]([CH2:13][OH:14])=[CH:9][CH:8]=2)[CH:2]=1.C[N+]1([O-])CCOCC1>[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]=[O:14])=[CH:9][CH:8]=2)[CH:2]=1

Participants

4

Reactant 2

HCID 82029Methyl morpholine oxideHCID 1515243[4-(Pyridin-3-yl)phenyl]methanol

Product 1

HCID 36930464-(Pyridin-3-yl)benzaldehydeYield 56.6%

Reagents, catalysts & solvents 1

HCID 178419074HCID 178419074, compoundCatalyst

Procedure

To a solution of (4-pyridin-3-yl-phenyl)-methanol (20 mg in 1.0 mL methylene chloride) was added 25 mg 4-methylmorpholine N-oxide, 20 mg 4 Å molecular sieves and 4 mg tetrapropylammonium perruthenate and the mixture stirred at room temperature. After 2 hours, the mixture was applied to a silica gel column and purified by flash chromatography (hexane:ethyl acetate, 40:60; then 60:40) to give the title compound (11.2 mg).

Workup

  1. custompurified by flash chromatography (hexane

Sources & evidence

ORD record
ord-5b144ce7c804459496db732284f83280
Source dataset
uspto-grants-1999_11
Patent number
US05985901

Reaction notes

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