Methyl morpholine oxide → 1-[3-(Benzyloxy)-6-chloropyridin-2-yl]ethanone

HRID 2091259Notes

Reaction equation

HRID 2091259 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([CH:16]([OH:18])[CH3:17])=[N:11][C:12]([Cl:15])=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[N+]1([O-])CCOCC1>[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC.C(#N)C>[CH2:1]([O:8][C:9]1[C:10]([C:16](=[O:18])[CH3:17])=[N:11][C:12]([Cl:15])=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 866627431-[3-(Benzyloxy)-6-chloropyridin-2-yl]ethanol

Product 1

HCID 866627441-[3-(Benzyloxy)-6-chloropyridin-2-yl]ethanoneYield 90%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

To a mixture of 1-[3-(benzyloxy)-6-chloropyridin-2-yl]ethanol (7.04 g) synthesized above, 4-methylmorpholine N-oxide (6.26 g) and acetonitrile (140 mL) was added tetrapropylammonium perruthenate (938 mg), and the mixture was stirred at room temperature for 3 hr, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (0-10% ethyl acetate/hexane) to give the title object compound (6.26 g, 90%) as a white solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified by silica gel column chromatography (0-10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-8b334ee8542244f490ec2f6b052640fd
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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