Ammonium Chloride → trans-3-[2-Benzyloxy-4-(1,1-dimethylheptyl)phenyl]-5-methylcyclohexanone
Reaction equation
[Li].[CH3:2][Cu]C.[CH2:5]([O:12][C:13]1[CH:18]=[C:17]([C:19]([CH3:27])([CH3:26])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH:16]=[CH:15][C:14]=1[CH:28]1[CH2:33][C:32](=[O:34])[CH:31]=[CH:30][CH2:29]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[Cl-].[NH4+]>CCOCC.CCCCCC>[CH2:5]([O:12][C:13]1[CH:18]=[C:17]([C:19]([CH3:26])([CH3:27])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH:16]=[CH:15][C:14]=1[C@H:28]1[CH2:29][C@H:30]([CH3:2])[CH2:31][C:32](=[O:34])[CH2:33]1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
To a 0° C. solution of dimethyl copper lithium (2.47 mmole) in ether (3 ml) and hexane (2 ml) was added dropwise a solution of 5-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-2-cyclohexen-1-one (500 mg, 1.24 mmole) in ether (1.5 ml). The reaction mixture was stirred for 15 minutes and then poured into saturated aqueous ammonium chloride (300 ml). The quenched reaction was extracted with three 50 ml portions of ether, the combined ether extracts washed with water, saturated sodium chloride, dried over magnesium sulfate and evaporated to yield 475 mg (92%) of the title compound as an oil.
Workup
- customThe quenched reaction
- extractionwas extracted with three 50 ml portions of ether
- washthe combined ether extracts washed with water, saturated sodium chloride
- dry with materialdried over magnesium sulfate
- customevaporated
Sources & evidence
- ORD record
- ord-ee91248379384f91988329a19e9e3f4f
- Source dataset
- uspto-grants-1983_07
- Patent number
- US04391827
Reaction notes
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