Ammonium Chloride → 2-(2'-Fluoro-5'-methoxy-4-((4-methoxybenzyl)oxy)biphenyl-2-yl)-3,3-dimethylbutan-2-ol
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)=[CH:12][C:11]=1[C:26](=[O:31])[C:27]([CH3:30])([CH3:29])[CH3:28].[CH3:32][Li].[Cl-].[NH4+]>C1COCC1.C(OCC)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)=[CH:12][C:11]=1[C:26]([OH:31])([C:27]([CH3:28])([CH3:30])[CH3:29])[CH3:32]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
Under a nitrogen atmosphere, to a solution of 1-(2′-fluoro-5′-methoxy-4-((4-methoxybenzyl)oxy)biphenyl-2-yl)-2,2-dimethylpropan-1-one (275 mg) in THF (5 mL) was added a solution (1.1 M, 1.7 mL) of methyllithium in diethyl ether at −78° C., and the mixture was stirred for 16 hr while allowing the temperature to gradually rise to room temperature. To the reaction mixture was added saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (182 mg) as a colorless oil.
Workup
- customto gradually rise to room temperature
- extractionthe mixture was extracted with ethyl acetate
- washThe extract was washed with saturated brine
- dry with materialdried over anhydrous sodium sulfate
- customThe solvent was evaporated under reduced pressure
- customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)
Sources & evidence
- ORD record
- ord-f3192ae9668e42ab8f77dcea8fa80d85
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09382188B2
Reaction notes
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