tert-Butanol → 3-{4-[5-(4-Isobutyl-3-methyl-thiophen-2-yl)-[1,3,4]oxadiazol-2-yl]-2,6-dimethyl-phenoxy}-propane-1,2-diol

Participants

Reaction Steps

To a solution of 2-(4-allyloxy-3,5-dimethyl-phenyl)-5-(4-isobutyl-3-methyl-thiophen-2-yl)-[1,3,4]oxadiazole (181 mg crude, 0.4 mmol) in a mixture of acetone and water (15:1.5 mL) are added N-methylmorpholine-N-oxide (250 mg, 1.85 mmol) and, subsequently, 2.5% OsO4 in tert.-butanol (0.1 mL). The mixture is stirred at rt for 36 h. The mixture is quenched into diethyl ether (75 mL) and washed with 1M aq. NaOH (50 mL), 1M aq. HCl (30 mL) and brine (20 mL). The organic phase is dried (Na2SO4), filtered and evaporated. The residue is purified by TLC (SiO2, EA-heptane) to give 118 mg of 3-{4-[5-(4-isobutyl-3-methyl-thiophen-2-yl)-[1,3,4]oxadiazol-2-yl]-2,6-dimethyl-phenoxy}-propane-1,2-diol as a white powder; LC-MS: tR=1.00 min, [M+1]+=417.28; 1H NMR (D6-DMSO): δ, 7.70 (s, 2 H) 7.51 (s, 1 H), 4.96 (d, J=5.0 Hz, 1 H), 4.63 (t, J=5.6 Hz, 1 H), 3.68-3.89 (m, 3 H), 3.47 (t, J=5.6 Hz, 2 H), 2.51 (s, 3 H), 2.45 (m, 2 H), 2.33 (s, 6 H), 1.85 (m, 1 H), 0.90 (d, J=6.7 Hz, 6 H).

Provenance & Evidence