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Dimethylformamide → 3-(2-Cyano-4-{2-[5-methyl-2-(4-phenoxyphenyl)oxazol-4-yl]ethoxy}phenyl)propionic acid ethyl ester

HRID 1181100
ノート
印刷プレビュー

反応式

HRID 1181100 の反応式
[CH2:1]([O:3][C:4](=C)[CH2:5][CH2:6][C:7]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][C:8]=1[C:9]#[N:10])[CH3:2].[CH3:17][C:18]1[O:22][C:21]([C:23]2[CH:28]=[CH:27][C:26]([O:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:25][CH:24]=2)=[N:20][C:19]=1[CH2:36][CH2:37]OS(C1C=CC(C)=CC=1)(=O)=O.CN(C=[O:53])C>CCOC(C)=O>[CH2:1]([O:3][C:4](=[O:53])[CH2:5][CH2:6][C:7]1[CH:14]=[CH:13][C:12]([O:15][CH2:37][CH2:36][C:19]2[N:20]=[C:21]([C:23]3[CH:28]=[CH:27][C:26]([O:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[CH:25][CH:24]=3)[O:22][C:18]=2[CH3:17])=[CH:11][C:8]=1[C:9]#[N:10])[CH3:2]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 179843252-(3-Ethoxy-but-3-enyl)-5-hydroxy-benzonitrileHCID 59759494Toluene-4-sulfonic acid 2-[5-methyl-2-(4-phenoxy-phenyl)-oxazol-4-yl]-ethyl ester

生成物 1

HCID 692321723-(2-Cyano-4-{2-[5-methyl-2-(4-phenoxyphenyl)oxazol-4-yl]ethoxy}phenyl)propionic acid ethyl ester

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate
溶媒

反応条件

温度
60 °C

実験手順

A mixture of 2-(3-ethoxy-but-3-enyl)-5-hydroxy-benzonitrile (220 mg, 1.00 mmol), toluene-4-sulfonic acid 2-[5-methyl-2-(4-phenoxy-phenyl)-oxazol-4-yl]-ethyl ester (450 mg, 1.00 mmol; Preparation 6), and CsCO3 (978 mg, 3.00 mmol) in DMF (10 mL) was stirred overnight at 60° C. under an N2. The mixture was cooled, diluted with EtOAc (20 mL) and washed with brine (20 mL). The organic layer was dried (Na2SO4) and concentrated. The product mixture was purified by radial chromatography (10-70% EtOAc/hexanes) to give 3-(2-cyano-4-{2-[5-methyl-2-(4-phenoxyphenyl)oxazol-4-yl]ethoxy}phenyl)propionic acid ethyl ester (201 mg). A solution of this ester in EtOH (10 mL) and 5N NaOH (10 mL) was heated at 70° C. overnight, concentrated, acidified with 1N HCl, and extracted with EtOAc. The organic layer dried (Na2SO4) and concentrated to give the title compound (192 mg); MS [ES] m/z 469 (M+1).

後処理

  1. temperatureThe mixture was cooled
  2. washwashed with brine (20 mL)
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. concentrationconcentrated
  5. customThe product mixture was purified by radial chromatography (10-70% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-4fe4c4379d8c41e982f51e8494e310de
出典データセット
uspto-grants-2007_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07282501B2

反応ノート

読み込み中…

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