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Dimethylformamide → ethyl 3-[1-[2-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]ethyl]-3-phenyl-1H-pyrazol-4-yl]propionate

HRID 350130
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HRID 350130 반응식
[H-].[Na+].CN(C)C=O.[C:8]1([C:14]2[C:18]([CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:17][NH:16][N:15]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.CS(O[CH2:31][CH2:32][C:33]1[CH:38]=[CH:37][C:36]([O:39][CH2:40][C:41]2[N:42]=[C:43]([C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)[O:44][C:45]=2[CH3:46])=[CH:35][CH:34]=1)(=O)=O>O>[CH3:46][C:45]1[O:44][C:43]([C:47]2[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=2)=[N:42][C:41]=1[CH2:40][O:39][C:36]1[CH:35]=[CH:34][C:33]([CH2:32][CH2:31][N:16]2[CH:17]=[C:18]([CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:14]([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)=[N:15]2)=[CH:38][CH:37]=1
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참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 867604162-[4-(5-Methyl-2-phenyl-4-oxazolylmethoxy)phenyl]ethyl methanesulfonateHCID 178471160HCID 178471160, 화합물

생성물 1

HCID 69421756ethyl 3-[1-[2-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]ethyl]-3-phenyl-1H-pyrazol-4-yl]propionate수율 62%

시약·촉매·용매 1

HCID 962Water용매

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온도
0 °C

실험 절차

Sodium hydride (60%, oily, 170 mg) was added to an N,N-dimethylformamide solution (50 ml) of ethyl 3-(3-phenyl-1H-pyrazole-4-yl)propionate (890 mg) at 0° C., and this mixture was stirred at 0° C. for 30 minutes. 2-[4-(5-Methyl-2-phenyl-4-oxazolylmethoxy)phenyl]ethyl methane sulfonate (2.79 g) was added to the reaction mixture, which was stirred at 90° C. for 1 hour. The reaction mixture was poured into water, which was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4), then concentrated. The residue was subjected to silica gel column chromatography, and ethyl 3-[1-[2-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]ethyl]-3-phenyl-1H-pyrazol-4-yl]propionate (1.19 g, yield: 62%) was obtained as colorless crystals. This was recrystallized from ethyl acetate-hexane. Melting point: 81–82° C.

후처리

  1. stirringwas stirred at 90° C. for 1 hour
  2. extractionwas extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-74a83ad9c1ed47e786808b083d7e48eb
출처 데이터셋
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07179823B1

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