Tetrabutylammonium Fluoride → HCID 21188052, compound

HRID 1383583Notes

Reaction equation

HRID 1383583 reaction equation
[C:1]([C:3]1[C:7]([C:8]#[C:9][Si](C)(C)C)=[CH:6][N:5]([C:14]2[C:19]([Cl:20])=[CH:18][C:17]([O:21][C:22]([F:25])([F:24])[F:23])=[CH:16][C:15]=2[Cl:26])[N:4]=1)#[N:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>ClCCl.O1CCCC1>[C:1]([C:3]1[C:7]([C:8]#[CH:9])=[CH:6][N:5]([C:14]2[C:19]([Cl:20])=[CH:18][C:17]([O:21][C:22]([F:24])([F:23])[F:25])=[CH:16][C:15]=2[Cl:26])[N:4]=1)#[N:2]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 23227974HCID 23227974, compound

Product 1

HCID 21188052HCID 21188052, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 3-cyano-1-(2,6-dichloro-4-trifiuoromethoxyphenyl)4-trimethylsilylethynylpyrazole (2.691 g) in dichloromethane (25 ml) was added tetra-n-butylammonium fluoride (6.45 ml of a 1M solution in tetrahydrofuran). Stirring was continued for 30 minutes then the reaction mixture was partitioned between water and dichioromethane. The aqueous layer was separated and extracted twice with di-chloromethane. The combined organic layers were washed with brine, dried (Na2SO4) and evaporated. The residue was purified by column chromatography on silica gel eluting with dichloromethane: hexane (1:1). Combination and evaporation of suitable fractions provided the title compound as a white solid m.p. 95.2-96.0° C.

Workup

  1. customthe reaction mixture was partitioned between water and dichioromethane
  2. customThe aqueous layer was separated
  3. extractionextracted twice with di-chloromethane
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customThe residue was purified by column chromatography on silica gel eluting with dichloromethane: hexane (1:1)
  8. customCombination and evaporation of suitable fractions

Sources & evidence

ORD record
ord-7f9f0171189043c28d9502d1df15cc57
Source dataset
uspto-grants-2001_07
Patent number
US06255333B1

Reaction notes

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