Triacetoxyperiodinane → HCID 11051749, compound

Participants

Reaction Steps

As reported by Schinzer et al.104 Dess-Martin periodinane (3.23 g, 7.61 mmol, 1.2 equiv) was added to a solution of alcohol 75 (0.9 g, 6.34 mmol) in methylene chloride (12 ml). The mixture was stirred at room temperature for 15 min before it was subjected to flash column chromatography (10% EtOAc/hexanes) to furnish aldehyde 67 (0.745 g, 84%) as highly volatile colorless liquid: [α]22D=+11.8 (c=0.5, CHCl3); TLC Rf=0.64 (silica gel, 25% EtOAc/hexanes); 1H NMR (600 MHz, CDCl3) δ 9.57-9.56 (d, 3J=1.8 Hz, 1H), 4.661 (s, 1H), 4.62 (s, 1H), 2.34-2.28 (m, 1H), 2.01-1.95 (t, 3J=7.8 Hz, 2H), 1.69-1.62 (m, 4H), 1.48-1.27 (m, 3H), 1.06-1.04 (d, 3J=6.6 Hz, 3H); 13C NMR (100 MHz, CDCl3) δ 205.282, 145.420, 110.441, 46.390, 37.845, 30.20, 24.969, 22.444, 13.523.

Provenance & Evidence