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

HRID 915418노트

반응식

HRID 915418 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 165872Tetrabutylammonium Cyanide촉매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-ebc1a2f123e54a609fbcf9fefe146927
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07265149B2

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