Acetonitrile → [2-Methyl-5-(4-trifluoromethyl-phenyl)-2H-pyrazol-3-yl]-acetonitrile

HRID 915418ノート

反応式

HRID 915418 の反応式
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]1

参加物

6

反応物 4

HCID 6342AcetonitrileHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 210822245-chloromethyl-1-methyl-3-(4-trifluoromethyl-phenyl)-1H-pyrazole

生成物 1

HCID 69282787[2-Methyl-5-(4-trifluoromethyl-phenyl)-2H-pyrazol-3-yl]-acetonitrile収率 18%

試薬・触媒・溶媒 1

HCID 165872Tetrabutylammonium Cyanide触媒

実験手順

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.

後処理

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. washthe combined organic layers were washed with ice water/brine 1/1
  4. dry with materialdried over sodium sulfate
  5. customthe solvent was evaporated in vacuo
  6. customto give an orange oil which
  7. customwas purified by column chromatography (silica gel, n-heptane/AcOEt)

出典と根拠

ORDレコード
ord-ebc1a2f123e54a609fbcf9fefe146927
出典データセット
uspto-grants-2007_09
特許番号
US07265149B2

反応ノート

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