反応式
[Br:1][C:2]1[CH:3]=[C:4]([C:8]#[C:9][C:10]2[CH:14]=[CH:13][N:12]([Si](C(C)C)(C(C)C)C(C)C)[CH:11]=2)[CH:5]=[CH:6][CH:7]=1.[O-:25]S([O-])(=O)=O.[Mg+2].C([O-])(O)=O.[Na+].[O-][Mn](=O)(=O)=O.[K+].[OH2:42]>CC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([C:8](=[O:25])[C:9]([C:10]2[CH:14]=[CH:13][NH:12][CH:11]=2)=[O:42])[CH:5]=[CH:6][CH:7]=1参加物
7
実験手順
To a solution of 3-[(3-bromophenyl)ethynyl]-1-(triisopropylsilyl)-1H-pyrrole (2.7 g, 8.5 mmol) in acetone (100 mml) is added a solution of MgSO4 (1.53 g, 12.75 mmol) and NaHCO3 (316 mg, 3.76 mmol) in water (50 ml), followed by the addition of KMnO4 (2.68 g, 17 mmol) in one portion at room temperature. After refluxing for 5 h, the reaction mixture is cooled to room temperature and extracted with ether (2×50 mL), the combined organic extracts are dried over MgSO4. The crude material is purified flash chromatography (silica gel, EtOAc/hexane: 30/70 to 50/50) to afford the title compound as a yellow solid (42%). mp: 111-113° C. MS (−) ES: 276 (M−H)−.
後処理
- temperatureAfter refluxing for 5 h
- extractionextracted with ether (2×50 mL)
- dry with materialthe combined organic extracts are dried over MgSO4
- customThe crude material is purified flash chromatography (silica gel, EtOAc/hexane: 30/70 to 50/50)
出典と根拠
- ORDレコード
- ord-81eb66d0faf046609e9bbb330e8d1602
- 出典データセット
- uspto-grants-2008_08
- 特許番号
- US07417047B2
関連ノート
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