2-(4-Benzyloxy-3-ethyl-5-methyl-phenyl)-5-(4-isopropoxy-3-methyl-phenyl)-[1,3,4]oxadiazole → 2-Ethyl-4-[5-(4-isopropoxy-3-methyl-phenyl)-[1,3,4]oxadiazol-2-yl]-6-methyl-phenol

Participants

Reaction Steps

To a solution of 2-(4-benzyloxy-3-ethyl-5-methyl-phenyl)-5-(4-isopropoxy-3-methyl-phenyl)-[1,3,4]oxadiazole (1.25 g, 2.82 mmol) in THF (10 mL), Pd/C (100 mg, 10% Pd) in EtOH (10 mL) is added. The mixture is stirred at rt under 1 atmosphere of H2 for 16 h before the catalyst is removed by filtration. The filtrate is concentrated and separated by CC on silica gel eluting with heptane:EA 4:1 to 1:1 to give 2-ethyl-4-[5-(4-isopropoxy-3-methyl-phenyl)-[1,3,4]oxadiazol-2-yl]-6-methyl-phenol (0.79 g) as a greenish solid; LC-MS: tR=1.12 min, [M+1]+=353.17, 1H NMR (D6-DMSO): δ 9.02 (s br, 1H), 7.90-7.86 (m, 2H), 7.70-7.66 (m, 2H), 7.13 (d, J=9.4 Hz, 1H), 4.72 (hept, J=5.0^9 Hz, 1H), 2.65 (q, J=7.6 Hz, 2H), 2.26 (s, 3H), 2.20 (s, 3H), 1.31 (d, J=5.9 Hz, 6H), 1.17 (t, J=7.6 Hz, 3H).

Provenance & Evidence