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

HRID 377651Notes

Reaction equation

HRID 377651 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 (50 μl 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 saturated 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-260c24c538394ba9a37cf1d391c58a79
Source dataset
uspto-grants-2000_02
Patent number
US06028096

Reaction notes

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