Methyl morpholine oxide → HCID 22258790, compound

HRID 1767310Notes

Reaction equation

HRID 1767310 reaction equation
[CH3:1][O:2][C:3]1[CH:22]=[CH:21][C:6]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[C:10]=2[CH:18]([OH:20])[CH3:19])=[CH:5][CH:4]=1.C[N+]1([O-])CCOCC1>ClCCl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[C:10]=2[C:18](=[O:20])[CH3:19])=[CH:21][CH:22]=1

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 22258876HCID 22258876, compound

Product 1

HCID 22258790HCID 22258790, compoundYield 80.1%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.), stirred solution of 1-{2-[(4-methoxybenzyl)oxy]-6-nitro-phenyl}ethanol (0.20 g, 0.659 mmol) in dichloromethane (20 mL) were added molecular sieves 4A (1 g), N-methylmorpholine N-oxide (0.15 g, 1.319 mmol) and tetra-n-propylammonium perruthenate (0.01 g). The mixture was stirred at room temperature for 12 hrs. The reaction mixture was filtered on Celite®, and the filtrate was diluted with ethyl acetate. The organic phase was washed with saturated aqueous ammonium chloride solution and dried over Na2SO4, filtered and concentrated under reduced pressure to give 1-{2-[(4-methoxybenzyl)oxy]-6-nitrophenyl}ethanone as a white solid (0.159 g, yield; 80%). The residue was used for the next step without further purification.

Workup

  1. filtrationThe reaction mixture was filtered on Celite®
  2. additionthe filtrate was diluted with ethyl acetate
  3. washThe organic phase was washed with saturated aqueous ammonium chloride solution
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-08191e29330f42a0adb3eb4c220d1002
Source dataset
uspto-grants-2007_06
Patent number
US07232909B2

Reaction notes

Loading…