Triacetoxyperiodinane → HCID 24950840, compound

Participants

Reaction Steps

7-Phenyl-1-(2-(pyridin-2-yl)oxazol-5-yl)-heptan-1-ol (S2, 20 mg, 0.059) was dissolved in CH2Cl2 (4 mL) and Dess-Martin periodinane (1.5 equiv) was added. The mixture was stirred at room temperature for 2 h before silica gel was added and the reaction mixture was evaporated in vacuo to afford the crude ketone absorbed on silica gel. This mixture was subsequently purified by flash chromatography (SiO2, 10-50% EtOAc-hexanes) to yield the title compound (18 mg, 90%) as a white solid: 1H NMR (CDCl3, 500 MHz) δ 8.89 (s, 1H), 8.31 (d, 1H, J=8.0 Hz), 7.99-7.94 (m, 2H), 7.55-7.52 (m, 1H), 7.36-7.33 (m, 2H), 7.26-7.23 (m, 3H), 3.00 (t, 2H, J=7.5 Hz), 2.69 (t, 2H, J=7.5 Hz), 1.87-1.81 (m, 2H), 1.75-1.69 (m, 2H), 1.51-1.47 (m, 4H); 13C NMR (CDCl3, 125 MHz) δ 189.4, 162.6, 150.8, 150.7, 145.6, 143.1, 137.6, 134.7, 128.8, 128.7, 126.2, 126.0, 123.8, 39.7, 36.3, 31.7, 29.4 (2C), 24.1; HRMS-ESI-TOF m/z 335.1750 ([M+H]+, C21H22N2O2 requires 335.1754). 1,3,4-Oxadiazoles (4a-4-d, 8a-8h, 20, 27-30) and 1,2,4-Oxadiazoles (9a-9g, 21-24): General Procedure A.

Provenance & Evidence