Methyl morpholine oxide → Ethyl 4-oxocyclohexanecarboxylate

HRID 1987237Notes

Reaction equation

HRID 1987237 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][CH:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]1.C[N+]1([O-])CCOCC1>C(#N)C.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[O:1]=[C:2]1[CH2:7][CH2:6][CH:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 86973Ethyl 4-hydroxycyclohexanecarboxylate

Product 1

HCID 317638Ethyl 4-oxocyclohexanecarboxylateYield 98%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

To a vigorously stirring suspension of ethyl 4-hydroxycyclohexanecarboxylate (2.0 g, 12 mmol, Aldrich) and activated 4 Å MS (1.0 g) in acetonitrile (70 mL) at 23° C. was sequentially added 4-methylmorpholine-N-oxide (2.0 g, 17 mmol) and tetrapropylammonium perruthenate (410 mg, 1.2 mmol). After stirring the resulting black suspension for 30 min, the mixture was concentrated in vacuo, and the resulting residue was filtered through a plug of silica gel (30% ethyl acetate in hexanes) to provide ethyl 4-oxocyclohexanecarboxylate as a clear oil (1.93 g, 98%). MS (AP CI) 171 (M+H).

Workup

  1. stirringAfter stirring the resulting black suspension for 30 min
  2. concentrationthe mixture was concentrated in vacuo
  3. filtrationthe resulting residue was filtered through a plug of silica gel (30% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-fe6098f77025429daf7d15d58398b835
Source dataset
uspto-grants-2009_06
Patent number
US07550500B2

Reaction notes

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