Methyl morpholine oxide → Ethyl 4-oxocyclohexanecarboxylate

HRID 412051Notes

Reaction equation

HRID 412051 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>[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC.C(Cl)Cl>[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 85%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 4-hydroxycyclohexanecarboxylate (16 g, 93 mmol), 4-methylmorpholine N-oxide (16.32 g, 139.5 mmol) and CH2Cl2 (180 mL) was added tetrapropylammonium perruthenate (0.8 g, 2.3 mmol) in small portions at a rate that maintained the reaction temperature at 35-40°. The reaction slowly cooled and was stirred overnight. The resulting mixture was filtered through silica with CH2Cl2 to afford 13.46 g (85%) of the title compound as a colorless oil. 1H NMR (CDCl3): d 4.19 (q, 2), 2.75 (m, 1), 2.5 (m, 2), 2.37 (m, 2), 2.19 (m, 2), 2.04 (m, 2).

Workup

  1. temperaturemaintained the reaction temperature at 35-40°
  2. customThe reaction
  3. temperatureslowly cooled
  4. filtrationThe resulting mixture was filtered through silica with CH2Cl2

Sources & evidence

ORD record
ord-1bf1b2b6f4ef46f68ff8e7352925505f
Source dataset
uspto-grants-2003_05
Patent number
US06562832B1

Reaction notes

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