反応式
[CH3:1][C:2]1([CH3:26])[CH2:11][CH2:10][C:9](=[O:12])[C:8]2[CH:7]=[C:6](/[CH:13]=[CH:14]/[C:15]3[CH:25]=[CH:24][C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:17][CH:16]=3)[CH:5]=[CH:4][C:3]1=2.BrC[C:29]([O:31][CH2:32][CH3:33])=[O:30].[CH:34]1C=CC=CC=1>[Zn]>[CH3:26][C:2]1([CH3:1])[CH2:11][CH2:10][C:9]([OH:12])([C:29]([O:31][CH2:32][CH2:33][CH3:34])=[O:30])[C:8]2[CH:7]=[C:6](/[CH:13]=[CH:14]/[C:15]3[CH:16]=[CH:17][C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:24][CH:25]=3)[CH:5]=[CH:4][C:3]1=2参加物
5
反応物 3
生成物 1
試薬・触媒・溶媒 1
実験手順
To a refluxing solution of 0.75 g (11.5 mmol) of granular zinc in 5.0 mL of benzene was added a solution of ethyl (E)-4-[2-(5,5-dimethyl-5,6,-dihydro-naphthalen-8(7H)-one-2-yl)ethenyl]-benzoate (Compound A2) in 5.0 mL of benzene followed by 0.27 g (0.18 mmol) of ethyl bromoacetate. The resulting mixture was refluxed for 24 h. The reaction was cooled, filtered through celite. The filtrate was washed with 10% HCl, sat. aqueous NaHCO3 and brine. The organic phase was dried over Na2SO4 and concentrated in vacuo. The crude material was purified by flash chromatography (silica, 10% ethyl acetate in hexane) to afford the title compound as a white solid.
後処理
- temperatureThe resulting mixture was refluxed for 24 h
- temperatureThe reaction was cooled
- filtrationfiltered through celite
- washThe filtrate was washed with 10% HCl, sat. aqueous NaHCO3 and brine
- dry with materialThe organic phase was dried over Na2SO4
- concentrationconcentrated in vacuo
- customThe crude material was purified by flash chromatography (silica, 10% ethyl acetate in hexane)
出典と根拠
- ORDレコード
- ord-360b2a9c7ec74d42ab635b936c6b9bb4
- 出典データセット
- uspto-grants-1998_05
- 特許番号
- US05747542
関連ノート
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