Methyl morpholine oxide → 2-Methyl-3-(4-methylphenyl)-2-pyridin-3-ylpropanal

HRID 1860667Notes

Reaction equation

HRID 1860667 reaction equation
[CH3:1][C:2]([C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1)([CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=1)[CH2:3][OH:4].C[N+]1([O-])CCOCC1>[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[CH3:1][C:2]([C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1)([CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=1)[CH:3]=[O:4]

Participants

4

Reactant 2

HCID 82029Methyl morpholine oxide2×HCID 186242042-Methyl-3-(4-methylphenyl)-2-pyridin-3-ylpropan-1-ol

Product 1

HCID 186241672-Methyl-3-(4-methylphenyl)-2-pyridin-3-ylpropanal

Reagents, catalysts & solvents 1

HCID 178419074HCID 178419074, compoundCatalyst2×

Procedure

A mixture of the product of STEP 3 (4.1 g, 16 mmol), N-methyl morpholine-N-oxide (2.9 g, 25 mmol), dry molecular sieves (8 g) and methylene chloride (35 ml) was stirred at room temperature for 15 min. Tetrapropylammoniumperruthenate (281 mg, 0.8 mmol) was added. The reaction was monitored by TLC, an additional N-methyl morpholine-N-oxide (0.73 g, 6.3 mmol), dry molecular sieves (2 g), and tetrapropylammoniumperruthenate (70.3 mg, 0.2 mmol) were added. After 2.5 h, the reaction mixture was filtered through a short column of Celite®. The filtrate was concentrated. The residue was purified by chromatography (on silica gel, ethyl acetate/hexane=4/1) to give a pale brown liquid in 1.66 g. NMR spectra of the product were consistent for the proposed structure.

Workup

  1. dry with materialdry molecular sieves (8 g) and methylene chloride (35 ml)
  2. additionwere added
  3. waitAfter 2.5 h
  4. filtrationthe reaction mixture was filtered through a short column of Celite®
  5. concentrationThe filtrate was concentrated
  6. customThe residue was purified by chromatography (on silica gel, ethyl acetate/hexane=4/1)
  7. customto give a pale brown liquid in 1.66 g

Sources & evidence

ORD record
ord-c7e653a3eb7a4dabb52280be357e62a8
Source dataset
uspto-grants-2003_03
Patent number
US06531494B1

Reaction notes

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