Water → HCID 22013563, compound

HRID 1532574Notes

Reaction equation

HRID 1532574 reaction equation
[F:1][C:2]1[C:3]([C:11]2[C:15]([Cl:16])=[C:14]([O:17][CH:18]([F:20])[F:19])[N:13]([CH3:21])[N:12]=2)=[N:4][C:5]([CH:9]=C)=[C:6]([Cl:8])[CH:7]=1.[O:22]1CCOCC1.O.[O-]I(=O)(=O)=O.[Na+]>C(OCC)(=O)C.[Os](=O)(=O)(=O)=O>[F:1][C:2]1[C:3]([C:11]2[C:15]([Cl:16])=[C:14]([O:17][CH:18]([F:20])[F:19])[N:13]([CH3:21])[N:12]=2)=[N:4][C:5]([CH:9]=[O:22])=[C:6]([Cl:8])[CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 312751,4-DioxaneHCID 23667635Sodium periodateHCID 59946906HCID 59946906, compound

Product 1

HCID 22013563HCID 22013563, compound

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

13.2 g of 3-(3-fluoro-5-chloro-6-vinyl-2-pyridyl)-4-chloro-5-difluoromethoxy-1-methyl-[1 H]-pyrazole (Example H35) are initially introduced into a mixture of 120 ml of dioxane and 40 ml of water. 16.7 g of sodium (meta)periodate (NalO4) and a spatula-tip of osmium tetroxide are added, while stirring, and the mixture is subsequently stirred overnight at 22° C. The following day, the resulting mixture is taken up in ethyl acetate and washed first with dilute hydrochloric acid and then with brine. After drying over sodium sulfate, the mixture is filtered and the filtrate is concentrated in vacuo. After purification over a silica gel flash column (eluting agent: n-hexane/ethyl acetate 2/1), 9.4 g of the desired title compound are obtained as a white solid of melting point 120-121° C.

Workup

  1. washwashed first with dilute hydrochloric acid
  2. dry with materialAfter drying over sodium sulfate
  3. filtrationthe mixture is filtered
  4. concentrationthe filtrate is concentrated in vacuo
  5. customAfter purification
  6. washover a silica gel flash column (eluting agent: n-hexane/ethyl acetate 2/1), 9.4 g of the desired title compound
  7. customare obtained as a white solid of melting point 120-121° C.

Sources & evidence

ORD record
ord-da3aea18cdbd44249d621a82c23a88a9
Source dataset
uspto-grants-2001_03
Patent number
US06204221B1

Reaction notes

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