p-Toluenesulfonic acid → 1-(4,5-Diphenyloxazol-2-yl)-8-(3-methoxybenzyl)-1-cyclooctene
Reaction equation
O[C:2]1([C:19]2[O:20][C:21]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[C:22]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[N:23]=2)[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[C:24]1([C:22]2[N:23]=[C:19]([C:2]3[CH:3]([CH2:10][C:11]4[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=4)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]=3)[O:20][C:21]=2[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1Participants
4
Procedure
A mixture of 1-(hydroxy)-1-(4,5-diphenyloxazol-2-yl)-2-(3-methoxybenzyl)cyclooctane (3.5 g) and p-toluenesulfonic acid (500 mg) in toluene (50 ml) was stirred for 4 hours under reflux. The solution was washed with water, sat. NaHCO3, and brine, dried over MgSO4, and evaporated in vacuo. The residue was purified by chromatography on silica gel to afford 1-(4,5-diphenyloxazol-2-yl)-8-(3-methoxybenzyl)-1-cyclooctene (3.8 g). MS (m/z): 450 (M+ +1) IR (Neat): 1600 cm-1NMR (CDCl3, δ): 1.4-2.0.(8H, m), 2.2-2.4 (2H, m), 3.0 (1H, m), 3.2-3.5 (2H, m), 3.78 (3H, s), 6.65 (1H, s), 6.7-7.0 (3H, m), 7.18 (1H, t, J=8 Hz), 7.2-7.8 (11H, m)