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Dimethylformamide → ethyl {4-[4-({4-[({4-[(Z)-2-(1-ethyl-1H-imidazol-5-yl)ethenyl]-1-phenyl-1H-pyrazol-3-yl}oxy)methyl]-2-methoxyphenoxy}methyl)-5-methyl-1,3-oxazol-2-yl]phenyl}acetate

HRID 2222006
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HRID 2222006 반응식
[CH:1]([C:3]1[C:4]([O:14][CH2:15][C:16]2[CH:42]=[CH:41][C:19]([O:20][CH2:21][C:22]3[N:23]=[C:24]([C:29]4[CH:34]=[CH:33][C:32]([CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])=[CH:31][CH:30]=4)[O:25][C:26]=3[CH2:27]C)=[C:18]([O:43][CH3:44])[CH:17]=2)=[N:5][N:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:7]=1)=O.Cl.[Cl-].[CH2:47]([N:49]1[C:53]([CH2:54][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:52][N:51]=[CH:50]1)[CH3:48].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH2:47]([N:49]1[C:53](/[CH:54]=[CH:1]\[C:3]2[C:4]([O:14][CH2:15][C:16]3[CH:42]=[CH:41][C:19]([O:20][CH2:21][C:22]4[N:23]=[C:24]([C:29]5[CH:30]=[CH:31][C:32]([CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])=[CH:33][CH:34]=5)[O:25][C:26]=4[CH3:27])=[C:18]([O:43][CH3:44])[CH:17]=3)=[N:5][N:6]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH:7]=2)=[CH:52][N:51]=[CH:50]1)[CH3:48]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 86605744[(1-ethyl-1H-imidazol-5-yl)methyl](triphenyl)phosphonium chloride hydrochlorideHCID 86605920ethyl (4-{4-[(4-{[(4-formyl-1-phenyl-1H-pyrazol-3-yl)oxy]methyl)-2-methoxyphenoxy)methyl]-5-ethyl-1,3-oxazol-2-yl}phenyl)acetate

생성물 1

HCID 86605919
ethyl {4-[4-({4-[({4-[(Z)-2-(1-ethyl-1H-imidazol-5-yl)ethenyl]-1-phenyl-1H-pyrazol-3-yl}oxy)methyl]-2-methoxyphenoxy}methyl)-5-methyl-1,3-oxazol-2-yl]phenyl}acetate
수율 20.3%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A mixture of ethyl (4-{4-[(4-{[(4-formyl-1-phenyl-1H-pyrazol-3-yl)oxy]methyl)-2-methoxyphenoxy)methyl]-5-ethyl-1,3-oxazol-2-yl}phenyl)acetate (2.00 g), [(1-ethyl-1H-imidazol-5-yl)methyl](triphenyl)phosphonium chloride hydrochloride (2.29 g), anhydrous potassium carbonate (1.78 g) and N,N-dimethylformamide (30 mL) was stirred at room temperature for 16 hrs. The reaction mixture was poured into water and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography and eluted with ethyl acetate-hexane (9:1 to 1:0, v/v) to give ethyl {4-[4-({4-[({4-[(Z)-2-(1-ethyl-1H-imidazol-5-yl)ethenyl]-1-phenyl-1H-pyrazol-3-yl}oxy)methyl]-2-methoxyphenoxy}methyl)-5-methyl-1,3-oxazol-2-yl]phenyl}acetate as colorless crystals (0.459 g, yield 20%). The crystals were recrystallized from tetrahydrofuran-hexane. melting point: 85-86° C.

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. washeluted with ethyl acetate-hexane (9:1 to 1:0

출처 및 근거

ORD 기록
ord-f9921329321c49358a02619290f56d8d
출처 데이터셋
uspto-grants-2008_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07368578B2

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