反応式
C([Li])CCC.Br[C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[N:13]=[C:12]([O:17][CH3:18])[CH:11]=[CH:10]2.[F:19][C:20]([F:30])([F:29])[C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[CH:24]=[O:25]>O1CCCC1>[CH3:18][O:17][C:12]1[CH:11]=[CH:10][C:9]2[C:14](=[CH:15][CH:16]=[C:7]([CH:24]([C:23]3[CH:26]=[CH:27][CH:28]=[C:21]([C:20]([F:19])([F:29])[F:30])[CH:22]=3)[OH:25])[CH:8]=2)[N:13]=1参加物
反応条件
- 温度
- -78 °C
実験手順
Butyllithium (12.5 ml) was added dropwise at -78° C. to a solution of 6-bromo-2-methoxyquinoline (4 g) in tetrahydrofuran (160 ml). After complete addition the mixture was stirred at -78° C. for 15 minutes. A solution of 3-(trifluoromethyl)-benzaldehyde (3.51 g) in tetrahydrofuran (40 ml) was added dropwise and the mixture was stirred at -78° C. for 30 minutes, then quenched with water (50 ml) and extracted with ethylacetate. The organic layer was separated, washed with brine, dried over MgSO4, filtered and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /CH3OH 97/3). The pure fractions were collected and the solvent was evaporated, yielding 3.7 g (66%) of (±)-2-methoxy-α-[3-(trifluoromethyl)phenyl]-6- quinoline methanol (intermediate 28).
後処理
- additionAfter complete addition the mixture
- stirringthe mixture was stirred at -78° C. for 30 minutes
- customquenched with water (50 ml)
- extractionextracted with ethylacetate
- customThe organic layer was separated
- washwashed with brine
- dry with materialdried over MgSO4
- filtrationfiltered
- customthe solvent was evaporated
- customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /CH3OH 97/3)
- customThe pure fractions were collected
- customthe solvent was evaporated
出典と根拠
- ORDレコード
- ord-68c86418cf27496893ae3caa1b9f8bff
- 出典データセット
- uspto-grants-1999_07
- 特許番号
- US05922734
関連ノート
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