Triacetoxyperiodinane → HCID 90408321, compound

Participants

Reaction Steps

To a 0° C. solution of 4-(1-(3-phenoxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)butan-1-ol (150 mg, 0.426 mmol) in DCM (3 mL) was added Dess-Martin periodinane (217 mg, 0.511 mmol) over 5 min. The reaction mixture was slowly warmed up to rt and stirred for 2 h. An aq. solution of saturated NaHCO3-Na2S2O3 was added, and the mixture was stirred at rt for 5 min. The organic layer was washed with brine, dried (MgSO4), and concentrated in vacuo. The crude product was purified by flash chromatography (SiO2; gradient from 0 to 40% EtOAc:hexanes) to afford the title compound as a white solid (120 mg, 80% yield). 1H NMR (400 MHz, CDCl3) δ 9.77 (t, J=1.5 Hz, 1H), 7.35-7.27 (m, 2H), 7.24 (s, 1H), 7.16-7.03 (m, 3H), 7.01-6.94 (m, 2H), 6.84 (ddd, J=8.0, 2.4, 1.0 Hz, 1H), 3.80 (s, 2H), 2.42 (td, J=7.3, 1.5 Hz, 2H), 2.07-1.96 (m, 4H), 1.76-1.55 (m, 6H), 1.23-1.10 (m, 2H).

Provenance & Evidence