Dimethylformamide dimethyl acetal → ethyl 1-tert-butyl-5-(4-fluorophenyl)-1H-pyrazole-4-carboxylate

HRID 1750339노트

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HRID 1750339 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.C[N:17]([CH:19](OC)OC)C.Cl.[C:25]([NH:29]N)([CH3:28])([CH3:27])[CH3:26]>C1(C)C=CC=CC=1>[C:25]([N:29]1[C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:19]=[N:17]1)([CH3:28])([CH3:27])[CH3:26]

참가 물질

5

반응물 3

HCID 78373Dimethylformamide dimethyl acetalHCID 81889tert-Butylhydrazine monohydrochlorideHCID 2758844Ethyl 3-(4-Fluorophenyl)-3-Oxopropanoate

생성물 1

HCID 86721178ethyl 1-tert-butyl-5-(4-fluorophenyl)-1H-pyrazole-4-carboxylate수율 68.3%

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
80 °C

실험 절차

A solution of ethyl 3-(4-fluorophenyl)-3-oxopropanoate (19.8 g, 94.20 mmol) and DMFDMA (13.76 mL, 103.61 mmol) in toluene (150 mL) was stirred at 100° C. for 14 hr, and concentrated under reduced pressure. The residue was dissolved in ethanol (150 ml), tert-butylhydrazine hydrochloride (11.74 g, 94.20 mmol) and TEA (14.44 mL, 103.61 mmol) were added thereto. The reaction mixture was stirred at 80° C. for 3 hr, and concentrated under reduced pressure. The residue was dissolved in ethyl acetate, and the solution was washed with water and saturated brine and dried, and the solvent was evaporated under reduced pressure to give ethyl 1-tert-butyl-5-(4-fluorophenyl)-1H-pyrazole-4-carboxylate (18.67 g, 64.3 mmol, 68.3%) as a white powder.

후처리

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in ethanol (150 ml)
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washthe solution was washed with water and saturated brine
  6. customdried
  7. customthe solvent was evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-43f56c01d8034bebbc80d86c8a398018
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09156837B2

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