Methyl morpholine oxide → 1-(6-Mesitylpyridin-2-yl)pentan-2-one

HRID 598110Notes

Reaction equation

HRID 598110 reaction equation
[C:1]1([CH3:21])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[C:9]1[N:14]=[C:13]([CH2:15][CH:16]([OH:20])[CH2:17][CH2:18][CH3:19])[CH:12]=[CH:11][CH:10]=1.C[N+]1([O-])CCOCC1>ClCCl.C(#N)C.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[C:1]1([CH3:21])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[C:9]1[N:14]=[C:13]([CH2:15][C:16](=[O:20])[CH2:17][CH2:18][CH3:19])[CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 2

HCID 82029Methyl morpholine oxideHCID 672670891-(6-Mesitylpyridin-2-yl)pentan-2-ol

Product 1

HCID 672671441-(6-Mesitylpyridin-2-yl)pentan-2-oneYield 30%

Reagents, catalysts & solvents 3

HCID 178419074HCID 178419074, compoundCatalystHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

1-(6-Mesitylpyridin-2-yl)pentan-2-ol (2.91 g, 10.3 mmol) in 100 mL of dichloromethane and 20 mL of acetonitrile was combined with 4 angstrom crushed molecular sieves (2.5 g) and N-methylmorpholine-N-oxide (1.80 g, 15.4 mmol). Tetrapropylammonium perruthenate (0.54 g, 1.54 mmol) was added last. The reaction stirred at room temperature for 1 h. The reaction was filtered and concentrated. Flash chromatography (10% ethyl acetate/hexanes) gave 0.87 g (30%) of the title compound as an yellow oil.

Workup

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-d16e864046794051a8f762f16773d8c8
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

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