反応式
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]([OH:21])[N:5]([C:12]([CH3:20])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH3:13])[C:6]2=[O:11].CN(CCN(C)C)C.C([Li])(CC)C.CCCCCC.[I:41]I.S([O-])([O-])(=O)=S.[Na+].[Na+]>C1COCC1>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([I:41])=[C:7]2[C:3]=1[CH:4]([OH:21])[N:5]([C:12]([CH3:13])([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[CH3:20])[C:6]2=[O:11]参加物
反応物 5
生成物 1
試薬・触媒・溶媒 1
実験手順
4-Chloro-3-hydroxy-2-(1-methyl-1-phenylethyl)isoindolinone (6.86 g, 22.7 mmol) was dissolved in THF (274 mL), and the solution was added with TMEDA (7.55 mL, 50.0 mmol), then added with sec-butyllithium-hexane solution (0.99 mol/L, 50.5 mL, 50.0 mmol) by drops at −78° C. over 20 minutes under argon atmosphere, followed by stirring at the same temperature for 2 hours. Then, the mixture was added with iodine (6.92 g, 27.3 mmol) and warmed from −78° C. to room temperature for 2.5 hours. The reaction mixture was added with 10% aqueous sodium thiosulfate solution and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by flash column chromatography (chloroform/methanol=100/0, 85/15) to obtain 4-chloro-3-hydroxy-7-iodo-2-(1-methyl-1-phenylethyl)isoindolinone (8.22 g, yield 85%).
後処理
- temperaturewarmed from −78° C. to room temperature for 2.5 hours
- extractionextracted with ethyl acetate
- washThe organic layer was washed with saturated brine
- dry with materialdried over anhydrous sodium sulfate
- customThe solvent was evaporated under reduced pressure
- customthe residue was purified by flash column chromatography (chloroform/methanol=100/0, 85/15)
出典と根拠
- ORDレコード
- ord-38562bcbda7b46d98c2c165e454b3966
- 出典データセット
- uspto-grants-2010_06
- 特許番号
- US07745641B2
関連ノート
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