Reaction equation
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]=1Participants
Conditions
- Temperature
- -78 °C
Procedure
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).
Workup
- 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
Sources & evidence
- ORD record
- ord-68c86418cf27496893ae3caa1b9f8bff
- Source dataset
- uspto-grants-1999_07
- Patent number
- US05922734
Linked notes
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