Methyl morpholine oxide → 2-(2-Chloro-5-methoxy-phenyl)-1-(2-chloro-pyridin-4-yl)-propan-1-one

HRID 1095950Notes

Reaction equation

HRID 1095950 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[CH:10]([CH3:20])[CH:11]([C:13]1[CH:18]=[CH:17][N:16]=[C:15]([Cl:19])[CH:14]=1)[OH:12].C[N+]1([O-])CCOCC1>C(Cl)Cl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[CH:10]([CH3:20])[C:11]([C:13]1[CH:18]=[CH:17][N:16]=[C:15]([Cl:19])[CH:14]=1)=[O:12]

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 866291052-(2-Chloro-5-methoxy-phenyl)-1-(2-chloro-pyridin-4-yl)-propan-1-ol

Product 1

HCID 866291062-(2-Chloro-5-methoxy-phenyl)-1-(2-chloro-pyridin-4-yl)-propan-1-oneYield 81.2%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

2-(2-Chloro-5-methoxy-phenyl)-1-(2-chloro-pyridin-4-yl)-propan-1-ol (140 mg) was dissolved in CH2Cl2 (20 mL). To this solution was added 3 Å molecular sieves (140 mg) and then tetrapropylammonium perruthenate (15.8 mg) and 4-methyl-morpholine-4-oxide (121 mg). The mixture was allowed to stir for 2 hours. The reaction mixture was applied directly to a silica gel column and the column was eluted with ethyl acetate:heptane=3:7. The appropriate fractions were combined and evaporated to give the title compound as a colorless gum (113 mg, 81%). MS (neg. ion, m/e)=308.4 [(M−H)−].

Workup

  1. additionTo this solution was added 3 Å molecular sieves (140 mg)
  2. washthe column was eluted with ethyl acetate
  3. customevaporated

Sources & evidence

ORD record
ord-106c8368d2f44995b1fb341ea42d86e5
Source dataset
uspto-grants-2012_03
Patent number
US08138189B2

Reaction notes

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