Ammonium Chloride → (2-Amino-5-{[tert-butyl(dimethyl)silyl]oxy}-phenyl)(phenyl)methanone
Reaction equation
[NH2:1][C:2]1[CH:13]=[CH:12][C:11]([O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])=[CH:10][C:3]=1[C:4](N(OC)C)=[O:5].[C:22]1([Mg]Br)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[Cl-].[NH4+]>O1CCCC1>[NH2:1][C:2]1[CH:13]=[CH:12][C:11]([O:14][Si:15]([C:18]([CH3:19])([CH3:20])[CH3:21])([CH3:16])[CH3:17])=[CH:10][C:3]=1[C:4]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:5]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 2-amino-5-{[tert-butyl(dimethyl)silyl]oxy}-N-methoxy-N-methylbenzamide (5.0 g, 16 mmol) in tetrahydrofuran (100 ml) was added dropwise 2.0 M solution (20 ml) of phenylmagnesium bromide in tetrahydrofuran at −78° C. The temperature of the reaction mixture was raised, and the mixture was stirred at room temperature for 30 min. Saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column to give (2-amino-5-{[tert-butyl(dimethyl)silyl]oxy}-phenyl)(phenyl)methanone (3.4 g, yield 65%) as a yellow oil.
Workup
- temperatureThe temperature of the reaction mixture was raised
- extractionthe mixture was extracted with ethyl acetate
- washThe extract was washed with saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
- customThe residue was purified by silica gel column
Sources & evidence
- ORD record
- ord-bf0e8f6b58e9471fbf797d5ee831fcce
- Source dataset
- uspto-grants-2009_06
- Patent number
- US07547710B2
Reaction notes
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