Methyl morpholine oxide → HCID 10399148, compound

HRID 2379538Notes

Reaction equation

HRID 2379538 reaction equation
[CH3:1]/[C:2](/[CH2:7][CH2:8]/[CH:9]=[C:10](\[CH3:17])/[CH2:11][CH2:12][CH:13]=[C:14]([CH3:16])[CH3:15])=[CH:3]\[CH2:4][CH2:5][OH:6].C[N+]1([O-])CCOCC1>C(#N)C.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[CH3:1]/[C:2](/[CH2:7][CH2:8]/[CH:9]=[C:10](\[CH3:17])/[CH2:11][CH2:12][CH:13]=[C:14]([CH3:16])[CH3:15])=[CH:3]\[CH2:4][CH:5]=[O:6]

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 10243212Homofarnesol

Product 1

HCID 10399148HCID 10399148, compoundYield 53.7%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6342AcetonitrileSolvent2×

Procedure

A solution of (E,E)-4,8,12-trimethyl-3,7,11-tridecatrienol (400 mg, 1.59 mmol) in acetonitrile (5 ml) was added to a slurry of N-methymorpholine N-oxide (280 mg, 2.38 mmol) and powdered 4A molecular sieves in acetonitrile (10 ml) and the mixture stirred at r.t. for 10 min. Tetrapropylammonium perruthenate (28 mg, 0.00795 mmol) was added in one portion and the resulting dark green slurry stirred at r.t for 1 hr. The reaction mixture was filtered through a plug of silica gel eluting with ethylacetate and the filtrate evaporated in vacuo. The resulting oil was chromatographed over silica gel eluting with diethylether:hexanes (1:10, v:v) to afford the title compound (200 mg, 50%) as a clear colorless oil.

Workup

  1. stirringthe resulting dark green slurry stirred at r.t for 1 hr
  2. filtrationThe reaction mixture was filtered through a plug of silica gel eluting with ethylacetate
  3. customthe filtrate evaporated in vacuo
  4. customThe resulting oil was chromatographed over silica gel eluting with diethylether:hexanes (1:10, v:v)

Sources & evidence

ORD record
ord-493ccca680974abc8ffc77287da3be43
Source dataset
uspto-grants-1994_11
Patent number
US05362906

Reaction notes

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