Hydrochloric Acid → 1-(4-Amino-3,5-dimethyl-phenyl)-2,2,2-trifluoro-1-(4-fluorophenyl)-ethanol
Reaction equation
[F:1][C:2]([F:30])([F:29])[C:3]([C:22]1[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=1)([C:5]1[CH:10]=[C:9]([CH3:11])[C:8]([N:12]([Si](C)(C)C)[Si](C)(C)C)=[C:7]([CH3:21])[CH:6]=1)[OH:4].Cl.[OH-].[Na+]>O1CCCC1>[NH2:12][C:8]1[C:9]([CH3:11])=[CH:10][C:5]([C:3]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)([OH:4])[C:2]([F:1])([F:29])[F:30])=[CH:6][C:7]=1[CH3:21]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
To a solution of 2,2,2-trifluoro-1-(4-fluoro-phenyl)-1-[4-(1,1,1,3,3,3-hexamethyl disilazan-2-yl)-3,5-dimethyl-phenyl]-ethanol (Example I2) (5 mmol) in tetrahydrofuran (15 ml) was added aqueous hydrochloric acid (concentrated) (1 ml) at 20° C. The reaction mixture was stirred at 20° C. for 15 hours. The reaction mixture was neutralized by addition of aqueous sodium hydroxide (4M). The mixture was extracted with diethyl ether. The organic phase was dried over sodium sulfate, filtered through a plug of silica gel and concentrated. The residue was triturated with heptane and a small amount of diethyl ether, then filtered and dried. The title compound was isolated as off-white crystals.
Workup
- customat 20° C
- extractionThe mixture was extracted with diethyl ether
- dry with materialThe organic phase was dried over sodium sulfate
- filtrationfiltered through a plug of silica gel
- concentrationconcentrated
- customThe residue was triturated with heptane
- filtrationa small amount of diethyl ether, then filtered
- customdried
Sources & evidence
- ORD record
- ord-73cadd65aa904144928d79a4b7175d74
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08618173B2
Reaction notes
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