Sodium ethoxide → 1-[4-(5-bromo-2-methoxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethylpentyl]-1H-quinolin-4-one
Reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:19][CH3:20])=[C:6]([C:8]([CH3:18])([CH3:17])[CH2:9][C:10]2([C:13]([F:16])([F:15])[F:14])[CH2:12][O:11]2)[CH:7]=1.[OH:21][C:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[N:25]=[CH:24][CH:23]=1.[O-]CC.[Na+]>C(O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:19][CH3:20])=[C:6]([C:8]([CH3:18])([CH3:17])[CH2:9][C:10]([OH:11])([C:13]([F:16])([F:15])[F:14])[CH2:12][N:25]2[C:26]3[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:22](=[O:21])[CH:23]=[CH:24]2)[CH:7]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 85 °C
Procedure
A mixture of 2-[2-(5-bromo-2-methoxyphenyl)-2-methylpropyl]-2-trifluoromethyloxirane (5.0 g, 14.2 mmol), 4-hydroxyquinoline (3.08 g, 21.2 mmol) and sodium ethoxide (21 wt. % solution in ethanol, 5.3 mL, 14.2 mmol) in ethanol (120 mL) was heated at 85° C. for 14 hours. The reaction was quenched with water and concentrated in vacuo to remove most of the ethanol. The residue was diluted with methylene chloride and washed with half saturated sodium bicarbonate (NaHCO3), dried over magnesium sulfate, filtered, and concentrated in vacuo. The product was precipitated from diethyl ether-hexanes to afford 1-[4-(5-bromo-2-methoxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethylpentyl]-1H-quinolin-4-one (5.2 g, 73% yield).
Workup
- customThe reaction was quenched with water
- concentrationconcentrated in vacuo
- customto remove most of the ethanol
- additionThe residue was diluted with methylene chloride
- washwashed with half saturated sodium bicarbonate (NaHCO3)
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe product was precipitated from diethyl ether-hexanes
Sources & evidence
- ORD record
- ord-6a9642b30b6244638165638edbbd6acf
- Source dataset
- uspto-grants-2009_08
- Patent number
- US07579469B2
Reaction notes
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