Water → HCID 58763926, compound

HRID 859180Notes

Reaction equation

HRID 859180 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:10]([CH:11]=C)=[C:9]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[N:8]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[Cl:26])[N:7]=1)=[O:5])[CH3:2].C[N+]1([O-])CC[O:31]CC1.O.I([O-])(=O)(=O)=O.[Na+]>O1CCOCC1.C(OCC)(=O)C.[Os](=O)(=O)(=O)=O>[CH2:1]([O:3][C:4]([C:6]1[C:10]([CH:11]=[O:31])=[C:9]([C:13]2[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=2)[N:8]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[Cl:26])[N:7]=1)=[O:5])[CH3:2]

Participants

8

Reactant 4

HCID 962WaterHCID 82029Methyl morpholine oxideHCID 23667635Sodium periodateHCID 42637618HCID 42637618, compound

Product 1

HCID 58763926HCID 58763926, compound

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 5-(4-chlorophenyl)-1-(2-chlorophenyl)-4-vinyl-1H-pyrazole-3-carboxylic acid ethyl ester I-1b (2.9 g, 7.5 mmol), osmium tetroxide (8 mg, 0.08 mmol) and N-methylmorpholine-N-oxide (1.1 g, 8.2 mmol) in dioxane (24 ml)/water (6 ml) was stirred at ambient temperature for 18 hours, then sodium periodate (16 g, 75 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 a solid mass. The solids were slurried in hot hexanes (30 ml), cooled, filtered and dried in vacuo to afford the title compound (I-1c) as a tan solid, 2.2 g.

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 a solid mass
  7. temperaturecooled
  8. filtrationfiltered
  9. customdried in vacuo

Sources & evidence

ORD record
ord-aa4bfc21b3844db7af7612e1b8e07423
Source dataset
uspto-grants-2006_12
Patent number
US07151097B2

Reaction notes

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