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

HRID 350305

반응식

HRID 350305 반응식
[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

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 5209941-(Chloromethyl)-4-phenoxybenzeneHCID 178469940HCID 178469940, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
90 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-8f7f8ede6a8d4eaca18ad63c178f6634
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07179823B1

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