Dimethylformamide → ethyl (2E)-3-[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-propenoate

HRID 2221989ノート

反応式

HRID 2221989 の反応式
[CH:1]([C:3]1[C:4]([O:14][CH2:15][C:16]2[CH:36]=[CH:35][C:19]([O:20][CH2:21][C:22]3[N:23]=[C:24](/[CH:28]=[CH:29]/[C:30]([O:32][CH2:33][CH3:34])=[O:31])[O:25][C:26]=3[CH3:27])=[C:18]([O:37][CH3:38])[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-].[CH2:40]([C:42]1[S:43][CH:44]=[C:45]([CH2:47][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[N:46]=1)[CH3:41].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH2:40]([C:42]1[S:43][CH:44]=[C:45](/[CH:47]=[CH:1]\[C:3]2[C:4]([O:14][CH2:15][C:16]3[CH:36]=[CH:35][C:19]([O:20][CH2:21][C:22]4[N:23]=[C:24](/[CH:28]=[CH:29]/[C:30]([O:32][CH2:33][CH3:34])=[O:31])[O:25][C:26]=4[CH3:27])=[C:18]([O:37][CH3:38])[CH:17]=3)=[N:5][N:6]([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH:7]=2)[N:46]=1)[CH3:41]

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 23076588[(2-Ethyl-1,3-thiazol-4-yl)methyl]triphenylphosphonium chlorideHCID 86605899ethyl (2E)-3-{4-[(4-([(4-formyl-1-phenyl-1H-pyrazol-3-yl)oxy]methyl}-2-methoxyphenoxy)methyl]-5-methyl-1,3-oxazol-2-yl}-2-propenoate

生成物 1

HCID 86605905ethyl (2E)-3-[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-propenoate収率 17%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A mixture of ethyl (2E)-3-{4-[(4-([(4-formyl-1-phenyl-1H-pyrazol-3-yl)oxy]methyl}-2-methoxyphenoxy)methyl]-5-methyl-1,3-oxazol-2-yl}-2-propenoate (0.87 g), [(2-ethyl-1,3-thiazol-4-yl)methyl]triphenylphosphonium chloride (1.06 g), anhydrous potassium carbonate (0.36 g) and N,N-dimethylformamide (50 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 (1:3, v/v) to give ethyl (2E)-3-[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-propenoate as colorless crystals (0.14 g, yield 17%). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 119-120° 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 (1:3

出典と根拠

ORDレコード
ord-7be63c44d76b4903a97512e99f406b99
出典データセット
uspto-grants-2008_05
特許番号
US07368578B2

反応ノート

読み込み中…