Methyl morpholine oxide → 1-[(1R)-4-Methylcyclohex-3-en-1-yl]-propan-1-one

HRID 735284Notes

Reaction equation

HRID 735284 reaction equation
[CH3:1][C:2]1[CH2:7][CH2:6][C@@H:5]([CH:8]=[O:9])[CH2:4][CH:3]=1.[CH2:10]([Mg]Br)[CH3:11].C[N+]1([O-])CCOCC1>[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[CH3:1][C:2]1[CH2:7][CH2:6][C@@H:5]([C:8](=[O:9])[CH2:10][CH3:11])[CH2:4][CH:3]=1

Participants

5

Reactant 3

HCID 82029Methyl morpholine oxideHCID 7367165(1R)-4-methylcyclohex-3-ene-1-carbaldehydeHCID 178418443HCID 178418443, compound

Product 1

HCID 578476511-[(1R)-4-Methylcyclohex-3-en-1-yl]-propan-1-one

Reagents, catalysts & solvents 1

HCID 178419074HCID 178419074, compoundCatalyst

Procedure

(1R)-4-Methyl-3-cyclohexene-1-carboxaldehyde was treated with ethylmagnesium bromide followed by tetrapropylammonium perruthenate and 4-methylmorpholine N-oxide to afford 1-[(1R)-4-methylcyclohex-3-en-1-yl]-propan-1-one; [α]D=+41.3 (c=1.0, CHCl3). The product was identical in all respects to the title compound.

Sources & evidence

ORD record
ord-83f253b03cf44160a001debe0d542819
Source dataset
uspto-grants-2009_09
Patent number
US07592463B2

Reaction notes

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