Acetonitrile → HCID 72269293, compound

HRID 1714500Notes

Reaction equation

HRID 1714500 reaction equation
[CH3:1][CH2:2][CH:3]([OH:12])[CH2:4][CH2:5][CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=[CH2:11].C(Cl)Cl.C[N+]1([O-])CCOCC1.C(#N)C>[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC.CCCCCC>[CH3:1][CH2:2][C:3](=[O:12])[CH2:4][CH2:5][CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=[CH2:11]

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 6344DichloromethaneHCID 82029Methyl morpholine oxide2×HCID 86642191HCID 86642191, compound

Product 1

HCID 72269293HCID 72269293, compoundYield 27%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalyst2×HCID 8058HexaneSolvent

Procedure

In argon atmosphere, 6,8,10-undecatrien-3-ol (5) (1.80 g, 10.8 mmol), methylene chloride (45 mL), Molecular Sieves 4A (4.50 g), N-methylmorpholine N-oxide (NMO) (1.90 g, 16.2 mmol) and acetonitrile (5 mL) were added to a 100 mL flask, and further tetrapropylammonium perruthenate (TPAP) (190 mg, 0.541 mmol) was added, followed by stirring at room temperature for 4 h. TPAP (190 mg, 0.541 mmol) was added, followed by stirring for 2 h at room temperature. Then NMO (1.90 g, 16.2 mmol) was added, followed by stirring for 3 h at room temperature. Hexane was added to the reaction mixture which then was filtered, and the filtrate was concentrated under reduced pressure. Thus obtained residue was purified on silica gel column chromatography (hexane:ethyl acetate=50:1) to give 6,8,10-undecatrien-3-one (1-1) (476 mg, 2.90 mmol, yield 27%).

Workup

  1. stirringby stirring for 2 h at room temperature
  2. stirringby stirring for 3 h at room temperature
  3. filtrationthen was filtered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThus obtained residue was purified on silica gel column chromatography (hexane:ethyl acetate=50:1)

Sources & evidence

ORD record
ord-351c2f8b451d41e58625ab62273fe929
Source dataset
uspto-grants-2010_09
Patent number
US07795474B2

Reaction notes

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