Methyl morpholine oxide → 4-Phenyl-3-furaldehyde

HRID 273956

Reaction equation

HRID 273956 reaction equation
[C:1]1([C:7]2[C:8]([CH2:12][OH:13])=[CH:9][O:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[N+]1([O-])CCOCC1>ClCCl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[C:1]1([C:7]2[C:8]([CH:12]=[O:13])=[CH:9][O:10][CH:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 15037154(4-Phenylfuran-3-yl)methanol

Product 1

HCID 150371484-Phenyl-3-furaldehyde

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-phenyl-3-furanmethanol (458 mg, 2.63 mmol), powdered 4A molecular sieves (500 mg), 4-methyl-morpholine-N-oxide (462 mg, 3.95 mmol) and tetrapropylammonium perruthenate (46 mg, 0.13 mmol) in anhydrous dichloromethane (40 ml) were stirred at room temperature for 3 hours. Residue was filtered through silica and concentrated to a brown oil which was purified by flash chromatography on silica using 10% ethyl ether/hexanes to give the titled aldehyde.

Workup

  1. filtrationResidue was filtered through silica
  2. concentrationconcentrated to a brown oil which
  3. customwas purified by flash chromatography on silica using 10% ethyl ether/hexanes

Sources & evidence

ORD record
ord-b1b35e12ac4a4ddebb35c5e5e2b4579a
Source dataset
uspto-grants-1995_02
Patent number
US05387606

Linked notes

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