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

HRID 2221931ノート

反応式

HRID 2221931 の反応式
C(C1CN([O:14][CH2:15][C:16]2[CH:39]=[CH:38][C:19]([O:20][CH2:21][C:22]3[N:23]=[C:24]([C:28]4[O:32][C:31]([C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:30][CH:29]=4)[O:25][C:26]=3[CH3:27])=[C:18]([O:40][CH3:41])[CH:17]=2)N(C2C=CC=CC=2)C=1)=O.[Cl-].[CH2:43]([C:45]1[S:46][CH:47]=[C:48]([CH2:50][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[N:49]=1)[CH3:44].C(=O)([O-])[O-].[K+].[K+].[CH3:76][N:77]([CH3:80])C=O>O>[CH2:43]([C:45]1[S:46][CH:47]=[C:48](/[CH:50]=[CH:27]\[C:26]2[C:22]([O:14][CH2:15][C:16]3[CH:39]=[CH:38][C:19]([O:20][CH2:21][C:22]4[N:23]=[C:24]([C:28]5[O:32][C:31]([C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:30][CH:29]=5)[O:25][C:26]=4[CH3:27])=[C:18]([O:40][CH3:41])[CH:17]=3)=[N:23][N:77]([C:80]3[CH:38]=[CH:39][CH:16]=[CH:17][CH:18]=3)[CH:76]=2)[N:49]=1)[CH3:44]

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 23076588[(2-Ethyl-1,3-thiazol-4-yl)methyl]triphenylphosphonium chlorideHCID 86605874ethyl 5-{4-[(4-{[(4-formyl-1-phenyl-1H-pyrazol-2-yl)oxy]methyl}-2-methoxyphenoxy)methyl]-5-methyl-1,3-oxazol-2-yl}-2-furancarboxylate

生成物 1

HCID 69215647ethyl 5-[4-({4-[({4-[(Z)-2-(2-ethyl-1,3-thiazol-4-yl)ethenyl]-1-phenyl-1H-pyrazol-3-yl}oxy)methyl]-2-methoxyphenoxy}methyl)-5-methyl-1,3-oxazol-2-yl]-2-furancarboxylate収率 32%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A mixture of ethyl 5-{4-[(4-{[(4-formyl-1-phenyl-1H-pyrazol-2-yl)oxy]methyl}-2-methoxyphenoxy)methyl]-5-methyl-1,3-oxazol-2-yl}-2-furancarboxylate (1.39 g), [(2-ethyl-1,3-thiazol-4-yl)methyl]triphenylphosphonium chloride (1.61 g), potassium carbonate (0.53 g) and N,N-dimethylformamide (30 mL) was stirred at room temperature for 15 hrs. Water was poured into the reaction mixture, 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 (1:1, v/v) to give ethyl 5-[4-({4-[({4-[(Z)-2-(2-ethyl-1,3-thiazol-4-yl)ethenyl]-1-phenyl-1H-pyrazol-3-yl}oxy)methyl]-2-methoxyphenoxy}methyl)-5-methyl-1,3-oxazol-2-yl]-2-furancarboxylate as colorless crystals (0.54 g, yield 32%). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 133-135° C.

後処理

  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 (1:1

出典と根拠

ORDレコード
ord-d51dba94503644719b603ea21e0c0bee
出典データセット
uspto-grants-2008_05
特許番号
US07368578B2

反応ノート

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