Methyl morpholine oxide → HCID 15074483, compound

HRID 2423224Notes

Reaction equation

HRID 2423224 reaction equation
[CH3:1][C:2]([C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=1)([CH3:5])[CH2:3][OH:4].C[N+]1([O-])CCOCC1>[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC.ClCCl>[CH3:5][C:2]([C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=1)([CH3:1])[CH:3]=[O:4]

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 222492792-Methyl-2-(4-nitrophenyl)propan-1-ol

Product 1

HCID 15074483HCID 15074483, compoundYield 55.2%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

In a 250 mL round bottom flask was charged 2-methyl-2-(4-nitrophenyl)propan-1-ol (3.86 g, 19.8 mmol), anhydrous dichloromethane (75 mL), 4-methylmorpholine N-oxide (3.47 g, 29.7 mmol), and 4 Å molecular sieves (9.8 g). TPAP (tetrapropylammonium perruthenate) (346 mg, 0.98 mmol) was added in one portion and the reaction was stirred at ambient temperature for 16 h. Upon completion of the reaction the material was filtered through a pad of silica and concentrated in vacuo. The material was purified by flash chromatography eluting with a gradient of 20% ethyl actetate/hexanes to 30% ethyl actetate/hexanes to give 2-methyl-2-(4-nitrophenyl)propanal (2.11 g, 55.1%).

Workup

  1. customUpon completion of the reaction the material
  2. filtrationwas filtered through a pad of silica
  3. concentrationconcentrated in vacuo
  4. customThe material was purified by flash chromatography
  5. washeluting with a gradient of 20% ethyl actetate/hexanes to 30% ethyl actetate/hexanes

Sources & evidence

ORD record
ord-40f5910bb0f44fc9aa0ba011715f084e
Source dataset
uspto-grants-2011_06
Patent number
US07960569B2

Reaction notes

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