[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:14][C:13](=[O:15])[NH:12][N:11]=2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[OH-:16].[Na+]>ClCCl.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:14][C:13](=[O:15])[N:12]([CH2:1][C:4]3[CH:9]=[CH:8][C:7]([C:10]([O:14][CH3:13])=[O:16])=[CH:6][CH:5]=3)[N:11]=2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2]5-(4-Isopropylphenyl)-1,3,4-oxadiazol-2(3H)-one (0.41 g, 2.0 mmol) is dissolved in dichloromethane (5 mL) and stirred vigorously with methyl 4-bromomethylbenoate (0.50 g, 2.2 mmol) in the presence of sodium hydroxide (1.25 N, 1.76 mL, 2.2 mmol) and tetra-n-butylammonium bromide (0.07 g, 0.022 mmol) at room temperature overnight. The solvent is removed in vacuum, and the residue is treated with water. The precipitate is collected by filtration, washed with hexanes thoroughly and dried in the air to provide methyl 4-{[5-(4-isopropylphenyl)-2-oxo-1,3,4-oxadiazol-3(2H)-yl]methyl}benzoate (0.65 g, 93%). (ES+): m/e 353.
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