[CH3:1][C:2]([NH:6][C:7](=[O:15])[C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1)([CH3:5])[C:3]#[CH:4]>[Cu]Cl.C(OCCCC)(=O)C>[Cl:14][C:11]1[CH:12]=[CH:13][C:8]([C:7]2[O:15][C:3](=[CH2:4])[C:2]([CH3:1])([CH3:5])[N:6]=2)=[CH:9][CH:10]=1A round bottom flask was charged with N-(3-methylbutyn-3-yl)-4-chlorobenzamide (4.5 g, 19.09 mmol), copper(I) chloride (9.5 mg, 0.5 mol %), and n-butyl acetate (20 mL). The resulting mixture was heated to 95° C. for 4 h, then cooled to room temperature. The reaction was washed with 1 M hydrochloric acid solution and with water. The organic layer was dried over anhydrous sodium sulfate. The solvent was removed by evaporation under reduced pressure, and the residue was dried in a vacuum oven to afford 2-(4-chlorophenyl)-4,4-dimethyl-5-methyleneoxazoline (4.24 g, 94% yield) as a pale yellow oil (bp 95° C., 0.6 mm Hg).
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