Sodium ethoxide → (E)-(4-Chlorophenyl)(cyclopropyl)methanone O-((2-methyl[biphenyl]-3-yl)methyl)oxime
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[C:8](/[CH:11]2[CH2:13][CH2:12]2)=[N:9]/[OH:10])=[CH:4][CH:3]=1.[O-]CC.[Na+].Cl[CH2:19][C:20]1[C:21]([CH3:32])=[C:22]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:23]=[CH:24][CH:25]=1>C(O)C>[CH3:32][C:21]1[C:20]([CH2:19][O:10]/[N:9]=[C:8](/[C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)\[CH:11]2[CH2:12][CH2:13]2)=[CH:25][CH:24]=[CH:23][C:22]=1[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
In a manner similar to General Procedure F of European Patent Publication No. 4,754, published Oct. 17, 1979, 1.96 g (0.01 mole) of (E)-(4-chlorophenyl)(cyclopropyl)methanone oxime was treated with 0.23 g (0.01 mole) of sodium ethoxide in 10 ml of ethanol, and the mixture was evaporated to dryness. The residue was dissolved in a minimum amount of solvent consisting of N,N-dimethylformamide and t-butanol (9:1 ratio) and treated with 2.16 g (0.01 mole) of 3-chloromethyl-2-methyl[1,1'-biphenyl] to yield, after purification by column chromatography, 0.83 g of (E)-(4-chlorophenyl)(cyclopropyl)methanone O-[(2-methyl[1,1'-biphenyl]-3-yl)methyl]oxime as an oil.
Workup
- customthe mixture was evaporated to dryness
- dissolutionThe residue was dissolved in a minimum amount of solvent
- customto yield
- customafter purification by column chromatography, 0.83 g of (E)-(4-chlorophenyl)(cyclopropyl)methanone O-[(2-methyl[1,1'-biphenyl]-3-yl)methyl]oxime as an oil
Sources & evidence
- ORD record
- ord-14b191e76e814b1caf7a0472ae11bb7d
- Source dataset
- uspto-grants-1984_02
- Patent number
- US04434182
Reaction notes
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