Ammonium Chloride → 1-Hydroxy-1-(3-fluoro-4-ethoxyphenyl)-2-(4-(4-propylcyclohexyl)cyclohexyl)ethane
Reaction equation
[F:1][C:2]1[CH:3]=[C:4](Br)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH3:10].[Mg].[CH2:13]([CH:16]1[CH2:21][CH2:20][CH:19]([CH:22]2[CH2:27][CH2:26][CH:25]([CH2:28][CH:29]=[O:30])[CH2:24][CH2:23]2)[CH2:18][CH2:17]1)[CH2:14][CH3:15].[Cl-].[NH4+]>C1COCC1>[OH:30][CH:29]([C:4]1[CH:5]=[CH:6][C:7]([O:8][CH2:9][CH3:10])=[C:2]([F:1])[CH:3]=1)[CH2:28][CH:25]1[CH2:26][CH2:27][CH:22]([CH:19]2[CH2:20][CH2:21][CH:16]([CH2:13][CH2:14][CH3:15])[CH2:17][CH2:18]2)[CH2:23][CH2:24]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
30 ml of a THF solution of 15.0 g (68.5 mmol) of 3-fluoro-4-ethoxybromobenzene was dropped under stirring to 1.8 g (75.4 mmol) of dried turnings magnesium at 40 to 60° C. Then, 100 ml of a THF solution of 22.3 g (89.1 mmol) of (4-(4-propylcyclohexyl)cyclohexyl)acetoaldehyde was dropped to the solution and stirred for 2 hours. The reaction mixture was poured into 100 ml of an aqueous saturated ammonium chloride solution and extracted with 200 ml of toluene. The organic layer was washed with 100 ml of water and then with 100 ml of aqueous saturated sodium chloride solution successively and, after drying over anhydrous magnesium sulfate, concentrated under a reduced pressure to obtain 25.9 g of crude 1-hydroxy-1-(3-fluoro-4-ethoxyphenyl)-2-(4-(4-propylcyclohexyl)cyclohexyl)ethane.
Workup
- extractionextracted with 200 ml of toluene
- washThe organic layer was washed with 100 ml of water
- dry with materialwith 100 ml of aqueous saturated sodium chloride solution successively and, after drying over anhydrous magnesium sulfate
- concentrationconcentrated under a reduced pressure
Sources & evidence
- ORD record
- ord-911447be88d44f98a7adb2d7f6386703
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07838087B2
Reaction notes
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