[Mg].[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]#[C:11][C:12]2[CH:17]=[CH:16][C:15](Br)=[CH:14][CH:13]=2)=[CH:6][CH:5]=1.N#N.II.[CH:23](N1CCCCC1)=[O:24].Cl>C1COCC1.O>[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]#[C:11][C:12]2[CH:17]=[CH:16][C:15]([CH:23]=[O:24])=[CH:14][CH:13]=2)=[CH:6][CH:5]=1To a dry 100 mL three-necked flask containing magnesium turnings (0.447 g; 18.38 mmol) in dry THF (8 mL), a small portion of 4-[(4-bromophenyl) ethynyl] phenyl methyl ether (VIIa) (0.300 g; 1.044 mmol) was added in one portion, at reflux under a flow of N2. N2 flow and stirring were stopped. The reaction mixture was heated at reflux for 5 minutes then iodine crystals were added, while reflux is maintained to start the reaction. A solution of remaining amount of 4-[(4-bromophenyl) ethynyl] phenyl methyl ether (VIIa) (4.5 g; 15.67 mmol) in dry THF (30 mL) was added drop wise into the reaction mixture while keeping gentle reflux. Reflux was maintained for 15 minutes then temperature was allowed to cool to RT under stirring for 1 h. The reaction mixture was cooled to 3° C. and a solution of dry 1-formyl-piperidine (2.8 mL; 25.07 mmol) in dry THF (10 mL) was added drop wise maintaining temperature at 5° C. The reaction mixture was then allowed to warm to RT and it was stirred overnight. The reaction mixture was cooled to 18° C. and 3N HCl (30 mL) was added. Water was added (50 mL) and extraction was performed with MTBE (50 mL×3). Organic phase was washed successively with water (50 mL×2), saturated solution of NaHCO3 (50 mL×1) and brine (50 mL×1). It was then dried over MgSO4, filtered and concentrated to give a yellow solid. It was taken up in Pet ether (40 mL) and left at 4° C. After 16 h the suspension was filtered and washed with Pet ether (2×30 mL) to give after drying under vacuum a clear yellow solid. The title compound was obtained (m=3.06 g) in a 77% yield. Melting point: 106° C.
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