Acetonitrile → [2-Methyl-5-(4-trifluoromethyl-phenyl)-2H-pyrazol-3-yl]-acetonitrile
Reaction equation
Cl[CH2:2][C:3]1[N:7]([CH3:8])[N:6]=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=2)[CH:4]=1.C(=O)(O)[O-].[Na+].C(OCC)(=O)C.[C:30](#[N:32])C>[C-]#N.C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:8][N:7]1[C:3]([CH2:2][C:30]#[N:32])=[CH:4][C:5]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=2)=[N:6]1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
Tetrabutylammonium cyanide (1.96 g, 7 mmol) was added to a solution of 5-chloromethyl-1-methyl-3-(4-trifluoromethyl-phenyl)-1H-pyrazole (1.54 g, 6 mmol) in acetonitrile (35 ml). The solution was stirred at ambient temperature for 16 h, saturated aqueous sodium bicarbonate solution/ice water 1/1 and ethyl acetate were added and the layers were separated. The aqueous layer was extracted with ethyl acetate, the combined organic layers were washed with ice water/brine 1/1, dried over sodium sulfate and the solvent was evaporated in vacuo to give an orange oil which was purified by column chromatography (silica gel, n-heptane/AcOEt) to yield 267 mg (1 mmol, 18%) of the title compound as yellow crystals.
Workup
- customthe layers were separated
- extractionThe aqueous layer was extracted with ethyl acetate
- washthe combined organic layers were washed with ice water/brine 1/1
- dry with materialdried over sodium sulfate
- customthe solvent was evaporated in vacuo
- customto give an orange oil which
- customwas purified by column chromatography (silica gel, n-heptane/AcOEt)
Sources & evidence
- ORD record
- ord-ebc1a2f123e54a609fbcf9fefe146927
- Source dataset
- uspto-grants-2007_09
- Patent number
- US07265149B2
Reaction notes
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