Triacetoxyperiodinane → HCID 24948914, compound

Participants

Reaction Steps

7-Phenyl-1-(2-(pyridin-2-yl)-2H-tetrazol-5-yl)-heptan-1-ol (2.7 mg, 0.007 mmol) was dissolved in CH2Cl2 (0.24 mL) and Dess-Martin periodinane (4.5 mg, 0.011 mmol) was added. The mixture was stirred at room temperature for 2 h before the reaction mixture was reduced to half volume and this mixture was directly loaded onto silica gel and purified by flash chromatography (SiO2, 0.5×4 cm, 10-30% EtOAc-hexanes) to afford 7-phenyl-1-(2-(pyridin-2-yl)-2H-tetrazol-5-yl)-heptan-1-one (15b, 2.7 mg, 99%) as a white solid: 1H NMR (CDCl3, 600 MHz) δ 8.74 (m, 1H), 8.23 (m, 1H), 8.05 (dt, 1H, J=1.6, 7.9 Hz), 7.57 (dd, 1H, J=4.8, 7.5 Hz), 7.27 (t, 2H, J=7.6 Hz), 7.17 (m, 3H), 3.26 (t, 2H, J=7.4 Hz), 2.61 (t, 2H, J=7.7 Hz), 1.83 (m, 2H), 1.64 (m, 2H), 1.43 (m, 4H); 13C NMR (CDCl3, 150 MHz) δ 191.5, 162.5, 149.9, 148.6, 142.8, 139.8, 128.5, 128.4, 126.0, 125.8, 115.9, 41.0, 36.0, 31.4, 29.1, 29.0, 23.5; HRMS-ESI-TOF m/z 336.1813 ([M+H]+, C19H21N5O requires 336.1819). Purity 99%.

Provenance & Evidence