反応式
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH:12]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH:29]=C)[C:13]([O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])=[O:14].[O:31]=[O+][O-]>C(Cl)Cl.CO>[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH:12]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH:29]=[O:31])[C:13]([O:15][CH2:16][CH2:17][Si:18]([CH3:19])([CH3:21])[CH3:20])=[O:14]参加物
5
反応物 2
生成物 1
試薬・触媒・溶媒 2
反応条件
- 温度
- -78 °C
実験手順
Dissolve 2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-(2-vinyl-phenyl)-propionic acid, 2-trimethylsilanyl-ethyl ester (2.61 g, 6.19 mmol) in methylene chloride (70 mL) and methanol (75 mL). Cool to -78° C. and treat with ozone until a blue color persists. Purge with nitrogen and add dimethylsulfide (7 mL) and pyridine (0.35 mL). Allow to warm to room temperature gradually overnight. Partition between methylene chloride (100 mL) and water (40 mL). Extract the aqueous with methylene chloride (50 mL), dry (Na2 SO4) and purify by silica gel chromatography (2.5:1 hexane/ethyl acetate) to give the title compound as a colorless viscous oil (2.65 g, 100%).
後処理
- customPurge with nitrogen
- additionadd dimethylsulfide (7 mL) and pyridine (0.35 mL)
- temperatureAllow to warm to room temperature gradually overnight
- customPartition between methylene chloride (100 mL) and water (40 mL)
- extractionExtract the aqueous with methylene chloride (50 mL)
- customdry (Na2 SO4)
- custompurify by silica gel chromatography (2.5:1 hexane/ethyl acetate)
出典と根拠
- ORDレコード
- ord-d5c09177d7e64c599435165854334fd6
- 出典データセット
- uspto-grants-1998_03
- 特許番号
- US05731306
関連ノート
読み込み中…