Hydrogen Peroxide → HCID 86698562, compound

Participants

Reaction Steps

To a solution of 80 mg (0.24 mmol) of aldehyde 31 in 3 mL of dichloromethane was added 1 mg (0.09 mmol) of SeO2 and 1.5 mL of H2O2 (30% in H2O). The reaction mixture was stirred at room temperature for 16 h then cooled to 0° C., 12 mL of 5% of NaHCO3 was added slowly. The mixture was stirred for additional 20 min then extracted with three portions of 15 mL of ethyl acetate. The combined organic layer was washed with brine and dried over Na2SO4. After solvent was removed, the residue was purified by flash chromatography on a silica gel column (15×2 cm). Elution with 1:10 EtOAc-hexanes gave product 32 as light yellow solid: yield 47.6 mg (57%). Silica gel TLC Rf 0.28 (4:1 EtOAc-hexanes); 1H NMR (CDCl3, ppm): δ 2.25 (s, 3H), 2.94 (s, 3H), 3.08 (t, J=8.4 Hz, 2H), 3.57 (t, J=8.4 Hz, 2H), 8.23 (s, 1H). 13C NMR (CDCl3, ppm): δ 19.21, 23.69, 32.36, 52.10, 113.38, 116.76, 119.95, 126.71, 150.24, 158.20, 162.82; 19F NMR (CDCl3, ppm): δ−73.77 (s, 3F); HRMS (ESI+) calculated for C11H11N2O5SF3 (M+H+) 340.0414. found 340.0413.

Provenance & Evidence