Dimethylformamide → ethyl 1-(4-phenoxybenzyl)-3-(4-phenoxybenzyloxy)-1H-pyrazole-4-carboxylate

HRID 350305

反応式

HRID 350305 の反応式
[OH:1][C:2]1[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][NH:4][N:3]=1.[O:12]([C:19]1[CH:26]=[CH:25][C:22]([CH2:23]Cl)=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[C:27](=[O:30])([O-])[O-].[K+].[K+].CN(C)C=O>O>[O:12]([C:19]1[CH:26]=[CH:25][C:22]([CH2:23][N:4]2[CH:5]=[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:2]([O:1][CH2:23][C:22]3[CH:21]=[CH:20][C:19]([O:30][C:27]4[CH:15]=[CH:14][CH:13]=[CH:18][CH:17]=4)=[CH:26][CH:25]=3)=[N:3]2)=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 5209941-(Chloromethyl)-4-phenoxybenzeneHCID 178469940HCID 178469940、化合物

生成物 1

HCID 23024849ethyl 1-(4-phenoxybenzyl)-3-(4-phenoxybenzyloxy)-1H-pyrazole-4-carboxylate収率 76.1%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
90 °C

実験手順

A mixture of ethyl 3-hydroxy-1H-pyrazole-4-carboxylate (8.95 g), 4-phenoxybenzyl chloride (25.35 g), potassium carbonate (31.88 g), and N,N-dimethylformamide (200 ml) was stirred at 90° C. for 8 hours. The reaction mixture was poured into water, and extracted with ethyl acetate. The ethyl acetate layer was washed successively with dilute hydrochloric acid and aqueous sodium chloride solution, dried (MgSO4), and concentrated. The residue was subjected to silica gel column chromatography to obtain ethyl 1-(4-phenoxybenzyl)-3-(4-phenoxybenzyloxy)-1H-pyrazole-4-carboxylate (22.71 g, yield: 76%) as a colorless oily substance from the fraction eluted with ethyl acetate-hexane (1:4, volume ratio).

後処理

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed successively with dilute hydrochloric acid and aqueous sodium chloride solution
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-8f7f8ede6a8d4eaca18ad63c178f6634
出典データセット
uspto-grants-2007_02
特許番号
US07179823B1

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