Triacetoxyperiodinane → HCID 90408321, compound

Participants

Reaction Steps

To a 0° C. solution of Example 57 compound [4-(1-(3-phenoxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)butan-1-ol] (110 mg, 0.312 mmol) in DCM (3 mL) was added Dess-Martin periodinane (159 mg, 0.375 mmol) over 5 min. The reaction mixture was slowly warmed up to rt and stirred at rt for 2 h. Sat′d aq. NaHCO3—Na2S2O3 was then added, and the reaction mixture was stirred at rt for 5 min. The layers were separated, and the organic layer was washed with water and brine, dried (MgSO4), filtered and concentrated in vacuo. The crude product was chromatographed (SiO2; continuous gradient of EtOAc/hexanes from 0 to 40%) to give the title compound as a white solid. (60 mg, 55% yield and 98% purity) 1H NMR (400 MHz, CDCl3) δ 9.80 (s, 1H), 7.41-7.32 (m, 3H), 7.32-7.27 (m, J=15.8 Hz, 1H), 7.20-7.07 (m, 1H), 7.05-6.98 (m, 1H), 6.87 (ddd, J=8.1, 2.5, 1.1 Hz, 1H), 3.83 (s, 2H), 2.46 (td, J=7.3, 1.5 Hz, 2H), 2.09-1.95 (m, 5H), 1.81-1.58 (m, 7H), 1.23-1.14 (m, 2H).

Provenance & Evidence