Methyl morpholine oxide → HCID 22926893, compound

HRID 1985292Notes

Reaction equation

HRID 1985292 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([CH2:11][CH:12]([O:18][CH:19]([CH3:21])[CH3:20])[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C[N+]1([O-])CCOCC1>ClCCl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[CH:2]([C:3]1[CH:4]=[C:5]([CH2:11][CH:12]([O:18][CH:19]([CH3:20])[CH3:21])[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10])=[O:1]

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 22494341HCID 22494341, compound

Product 1

HCID 22926893HCID 22926893, compoundYield 95.3%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

826 mg of Ethyl 3-[3-(hydroxymethyl)-4-methoxyphenyl]-2-isopropoxypropanoate was dissolved in 20 ml of dichloromethane, and 390 mg of N-methylmorpholine N-oxide, 1.4 g of molecular sieve 4A and 49 mg of tetrapropylammonium perruthenate were added, and the mixture was stirred at room temperature overnight. The reaction mixture was filtered through Celite, the filtrate was concentrated, and the residue was purified by silica gel column chromatography, to give 782 mg of the title compound in the 5:1→2:1 hexane-ethyl acetate fraction.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated
  3. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-841fd412c5b9445dac495fe481d7264f
Source dataset
uspto-grants-2009_06
Patent number
US07544835B2

Reaction notes

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