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Methyl morpholine oxide → HCID 58763943, compound

HRID 859185
Notes
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Reaction equation

HRID 859185 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:10]([O:11][CH2:12][CH:13]=C)=[C:9]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[N:8]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[Cl:28])[N:7]=1)=[O:5])[CH3:2].C[N+]1([O-])CC[O:33]CC1.I([O-])(=O)(=O)=O.[Na+]>O.O1CCOCC1.C(OCC)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[C:10]([O:11][CH2:12][CH:13]=[O:33])=[C:9]([C:15]2[CH:16]=[CH:17][C:18]([Cl:21])=[CH:19][CH:20]=2)[N:8]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[Cl:28])[N:7]=1)=[O:5])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 82029Methyl morpholine oxideHCID 23667635Sodium periodateHCID 58763935HCID 58763935, compound

Product 1

HCID 58763943HCID 58763943, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 8857
Ethyl Acetate
Solvent
HCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of 4-allyloxy-5-(4-chlorophenyl)-1-(2-chlorophenyl)-1H-pyrazole-3-carboxylic acid ethyl ester I-1e (337 mg, 0.8 mmol) osmium tetroxide (53 microliters of a 0.15 M solution in water) and N-methylmorpholine-N-oxide (120 mg, 0.9 mmol) in dioxane (2.4 ml)/water (0.6 ml) was stirred at ambient temperature for 18 hours, then sodium periodate (1.7 g, 8.1 mmol) was added and stirring was continued for 3.5 hours. The thick slurry was diluted with ethyl acetate (100 ml), filtered and solids washed 2× with ethyl acetate. The combined filtrates were washed with water, brine, dried (Na2SO4) and concentrated in vacuo to afford an oil. Silica gel chromatography (25% ethyl acetate/hexanes) afforded the title compound (I-1f) as a colorless foam, 130 mg.

Workup

  1. filtrationfiltered
  2. washsolids washed 2× with ethyl acetate
  3. washThe combined filtrates were washed with water, brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customto afford an oil

Sources & evidence

ORD record
ord-8044a58e722e4fbf970487ee56b6d4a3
Source dataset
uspto-grants-2006_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07151097B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes