1-Bromo-3-(trimethylsiloxy)benzene → 4-Hydroxy-4-(4-hydroxyphenyl)-7-(methoxymethoxy)-3-[4-(methoxymethoxy)phenyl]chroman
反応式
C[Si]([O:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8](Br)[CH:7]=1)(C)C.[Mg].[CH3:14][O:15][CH2:16][O:17][C:18]1[CH:38]=[CH:37][C:21]2[C:22](=[O:36])[CH:23]([C:26]3[CH:31]=[CH:30][C:29]([O:32][CH2:33][O:34][CH3:35])=[CH:28][CH:27]=3)[CH2:24][O:25][C:20]=2[CH:19]=1>O1CCCC1>[OH:5][C:6]1[CH:11]=[CH:10][C:9]([C:22]2([OH:36])[C:21]3[CH:37]=[CH:38][C:18]([O:17][CH2:16][O:15][CH3:14])=[CH:19][C:20]=3[O:25][CH2:24][CH:23]2[C:26]2[CH:31]=[CH:30][C:29]([O:32][CH2:33][O:34][CH3:35])=[CH:28][CH:27]=2)=[CH:8][CH:7]=1参加物
反応条件
- 温度
- -78 °C
実験手順
Under nitrogen atmosphere, 3-bromomagnesium phenyl trimethylsilyl ether prepared from 3-bromophenyl trimethylsilyl ether (2.35 g, 9.57 mmol) and magnesium turning (0.23 g, 9.57 mmol) in dry tetrahydrofuran (3 ml) was cooled to -78° C. 7-Methoxymethyloxy-3-[4-(methoxymethyloxy)phenyl]-2,3-dihydro-4H-benzopyran-4-one (1 g, 2.9 mmol) dissolved in dry tetrahydrofuran (2 ml) was slowly added dropwise thereto, and the mixture was stirred for one hour. The reaction solution was quenched with saturated aqueous ammonium chloride solution and then extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to remove the organic solvent. The concentrate was then subjected to column chromatography (n-hexane:ethyl acteate=4:1) to obtain 903 mg (yield: 74%) of the title compound as a foam.
後処理
- additionwas slowly added dropwise
- customThe reaction solution was quenched with saturated aqueous ammonium chloride solution
- extractionextracted with ethyl acetate
- dry with materialThe organic layer was dried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
- customto remove the organic solvent
出典と根拠
- ORDレコード
- ord-59b06c02bf3b40739e08419ca2b14e05
- 出典データセット
- uspto-grants-2000_11
- 特許番号
- US06153768
反応ノート
読み込み中…