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

HRID 1750339ノート

反応式

HRID 1750339 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-43f56c01d8034bebbc80d86c8a398018
出典データセット
uspto-grants-2015_10
特許番号
US09156837B2

反応ノート

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