Acetone → 3-Cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)4-formylpyrazole

HRID 1108823Notes

Reaction equation

HRID 1108823 reaction equation
[C:1]([C:3]1[C:7]([CH:8]=C)=[CH:6][N:5]([C:10]2[C:15]([Cl:16])=[CH:14][C:13]([C:17]([F:20])([F:19])[F:18])=[CH:12][C:11]=2[Cl:21])[N:4]=1)#[N:2].C[N+]1([O-])CC[O:26]CC1.CC(C)=O.I([O-])(=O)(=O)=O.[Na+]>C(O)(C)(C)C.O.[Os](=O)(=O)(=O)=O>[C:1]([C:3]1[C:7]([CH:8]=[O:26])=[CH:6][N:5]([C:10]2[C:15]([Cl:16])=[CH:14][C:13]([C:17]([F:20])([F:19])[F:18])=[CH:12][C:11]=2[Cl:21])[N:4]=1)#[N:2]

Participants

8

Reactant 4

HCID 180AcetoneHCID 82029Methyl morpholine oxideHCID 211880943-Cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-ethenylpyrazoleHCID 23667635Sodium periodate

Product 1

HCID 184179813-Cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)4-formylpyrazole

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

A solution of 3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-ethenylpyrazole (0.1 g), N-methylmorpholine oxide (0.005 g), osmium tetroxide (5011 of a 2.5% solution in t-butanol) in water (5 ml) and acetone (45 ml) was stirred at room temperature for 16 hours Sodium metaperiodate (0.005 g) was added and stirring continued for 16 hours. The reaction mixture was evaporated and the residue partititoned between ether and aqueous sodium hydrogen carbonate solution. The aqueous layer was separated and extracted with ether. The combined ether extracts were dried (Na2SO4) and evaporated. The residue was purified by column chromatography on silica gel (5 g) eluted with dichloromethane. Combination and evaporation of suitable fractions gave the title compound as a biege solid, m.p. 167.5-168.5° C.

Workup

  1. additionwas added
  2. customThe reaction mixture was evaporated
  3. customThe aqueous layer was separated
  4. extractionextracted with ether
  5. dry with materialThe combined ether extracts were dried (Na2SO4)
  6. customevaporated
  7. customThe residue was purified by column chromatography on silica gel (5 g)
  8. washeluted with dichloromethane
  9. customCombination and evaporation of suitable fractions

Sources & evidence

ORD record
ord-3ce7a98446e7487c8edfae9a0969ce85
Source dataset
uspto-grants-2000_05
Patent number
US06069157

Reaction notes

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