Triacetoxyperiodinane → HCID 57955235, compound

Participants

Reaction Steps

Dess-Martin periodinane (703.6 mg, 1.66 mmol) was added to a stirring solution of Example 62 (600 mg, 1.11 mmol) dissolved in DMSO (3 mL). After 1 hour HPLC indicated that the reaction was complete. The reaction was diluted with EtOAc (200 mL) washed with aq. Sodium thiosulfate solution (2M) (2×), and saturated NaHCO3 solution (2×). The organic layer was dried (Na2SO4) and concentrated to give a brown powder which was triturated with 10% Et2O/Hexanes to afford 450 mg (0.83 mmol, 75.3%) of the title compound. 1H-NMR (DMSO-d6). δ 10.00 (s, 1H), 9.95 (s, 1H), 9.84 (s, 1H), 8.60 (d, J=5.4 Hz, 1H), 8.12 (s, 1H), 8.07 (s, 1H), 7.89 (d, J=8.7 Hz, 2H), 7.49 (d, J=8.4 Hz, 2H), 7.43 (d, J=5.1 Hz, 1H), 4.18 (s, 2H), 3.57-3.54 (m, 4H), 2.55-2.51 MS [M+H]+=541; LCMS RT=2.50 min.

Provenance & Evidence