[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2([C:12]#[N:13])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1)#[CH:2].[O:14]1CCCC1.Cl[N:20]1C(=O)C[CH2:22][C:21]1=O.C(N(CC)CC)C>C(OCC)(=O)C>[CH3:22][C:21]1[C:1]([C:3]2[CH:8]=[CH:7][C:6]([C:9]3([C:12]#[N:13])[CH2:10][CH2:11]3)=[CH:5][CH:4]=2)=[CH:2][O:14][N:20]=1To a mixture of 1-(4-ethynylphenyl)cyclopropanecarbonitrile (200 mg, 0.001 mol) acetaldoxime (71 mg, 0.0012 mol) in tetrahydrofuran (5.0 mL, 0.062 mol) was added N-chlorosuccinimide (160 mg, 0.0012 mol) in portions with stirring. After the addition was complete, triethylamine (170 μL, 0.0012 mol) was added. The mixture was stirred at rt for 2 days. The reaction mixture was diluted with ethyl acetate and washed with water and brine successively, dried over MgSO4 and filtered. The filtrate was concentrated to afford the desired product in quantitative yield.
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