p-Toluenesulfonic acid → HCID 22591679, compound
Reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10]1[O:11][C:12]([C:15]23[CH2:22][CH2:21][C:18]([CH2:23][CH2:24][CH2:25][C:26]4([CH3:31])OCC[O:27]4)([CH2:19][CH2:20]2)[CH2:17][CH2:16]3)=[N:13][N:14]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10]1[O:11][C:12]([C:15]23[CH2:22][CH2:21][C:18]([CH2:23][CH2:24][CH2:25][C:26](=[O:27])[CH3:31])([CH2:19][CH2:20]2)[CH2:17][CH2:16]3)=[N:13][N:14]=1Participants
4
Procedure
2-(2-Chloro-4-methoxyphenyl)-5-{4-[3-(2-methyl-1,3-dioxolan-2-yl)propyl]bicyclo[2.2.2]oct-1-yl}-1,3,4-oxadiazole (5-G) (0.200 g) was stirred in a mixure of 90% acetone/10% water (20 mL). p-Toluenesulfonic acid (15 mg) was added to the solution. The reaction was heated to reflux for 1 h. The volume was reduced by evaporation of acetone in vacuo. The mixture was then layered with ethyl acetate (25 mL) and saturated sodium bicarbonate solution (25 mL). The ethyl acetate layer was extracted and dried (MgSO4). Solvent was removed in vacuo to afford pure 5-{4-[5-(2-chloro-4-methoxyphenyl)-1,3,4-oxadiazol-2-yl]bicyclo[2.2.2]oct-1-yl}pentan-2-one (5-H).