Methyl morpholine oxide → HCID 11116244, compound

HRID 1441029Notes

Reaction equation

HRID 1441029 reaction equation
[CH:1]1([CH2:7]/[CH:8]=[CH:9]/[CH2:10][OH:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C[N+]1([O-])CCOCC1>C(Cl)Cl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[CH:1]1([CH2:7]/[CH:8]=[CH:9]/[CH:10]=[O:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 11062610HCID 11062610, compound

Product 1

HCID 11116244HCID 11116244, compound

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To 10.2 g (65.93 mmol) of (E)-4-cyclohexyl-2-buten-1-ol dissolved in 700 mL of CH2Cl2 with 10 g crushed activated 4A molecular sieves was added 11.97 g (102.2 mmol) of N-methyl morpholine-N-oxide. This mixture was cooled to 0° C. and a catalytic amount 1.197 g (3.40 mmol) of tetrapropylammonium perruthenate was added slowly. After 18 hr the mixture was filtered through celite, concentrated in vacuo, and filtered through a plug of silica gel (6×6 cm 5% ether in hexanes) to provide the title compound as a colorless oil. Further purification by fractional distillation (bp 58°-60° C., 2 mm of Hg) afforded an oil.

Workup

  1. filtrationAfter 18 hr the mixture was filtered through celite
  2. concentrationconcentrated in vacuo
  3. filtrationfiltered through a plug of silica gel (6×6 cm 5% ether in hexanes)

Sources & evidence

ORD record
ord-a841fc4db0ea43d5b050e38e0b16b69f
Source dataset
uspto-grants-1996_03
Patent number
US05502053

Reaction notes

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