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

HRID 1274344Notes

Reaction equation

HRID 1274344 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 partitioned 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 beige solid, m.p. 167.5-168.5° C.

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue partitioned between ether and aqueous sodium hydrogen carbonate solution
  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-b362a5cd101f411fb3d08de5b67341d5
Source dataset
uspto-grants-2000_12
Patent number
US06156782

Reaction notes

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