Ammonium Chloride → 4-(3-Fluoro-4-methoxyphenyl)-4-hydroxy-1-phenylcyclohexanecarbonitrile
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([Mg]Br)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[O:12]=[C:13]1[CH2:18][CH2:17][C:16]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([C:19]#[N:20])[CH2:15][CH2:14]1.[Cl-].[NH4+]>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([C:13]2([OH:12])[CH2:18][CH2:17][C:16]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)([C:19]#[N:20])[CH2:15][CH2:14]2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]Participants
Procedure
Under an argon atmosphere, 15 ml of 3-fluoro-4-methoxyphenylmagnesium bromide solution (0.5 M in THF) were dissolved in 15 ml of dry THF in a dried two-necked flask equipped with a reflux condenser, and subsequently 1.5 g of 4-oxo-1-phenylcyclohexanecarbonitrile in the form of a suspension in 10 ml of THF were slowly added dropwise at room temperature. A precipitate was formed in the course of this. The reaction solution was heated under reflux for 2 h, subsequently added to ice water, treated with saturated ammonium chloride solution and extracted three times with EA. The combined organic phases were dried over magnesium sulfate and the solvent was removed in vacuo. The residue was purified chromatographically (HEP/EA 2:1) on silica gel. 950 mg of the title compound were obtained as a white solid.
Workup
- customequipped with a reflux condenser
- customA precipitate was formed in the course of this
- temperatureThe reaction solution was heated
- temperatureunder reflux for 2 h
- extractionextracted three times with EA
- dry with materialThe combined organic phases were dried over magnesium sulfate
- customthe solvent was removed in vacuo
- customThe residue was purified chromatographically (HEP/EA 2:1) on silica gel
Sources & evidence
- ORD record
- ord-2db24f1ec0d94b8da41144301aa5c38d
- Source dataset
- uspto-grants-2011_12
- Patent number
- US08076324B2
Reaction notes
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