Sodium Bicarbonate → HCID 86698561, compound

Participants

Reaction Steps

To a solution of 134 mg of alcohol 30 in 2 mL of DMSO and 2 mL of acetone was added 116 mg of IBX. The reaction mixture was stirred at room temperature for 16 h then cooled to 0° C., 5 mL of a mixture of 5% NaHCO3 and 5% of NaS2O3 was added by syringe slowly. After stirred for additional 20 min the mixture was extracted with three portions of 5 mL of ethyl acetate. The combined organic layer was washed with brine and dried over MgSO4. After the solvent was removed under diminished pressure, the residue was purified by flash chromatography on a silica gel column (15×2 cm). Elution with 1:10 EtOAc-hexanes gave product 31 as white crystal: yield 121 mg, (91%). Silica gel TLC Rf 0.20 (1:4 EtOAc-hexanes); 1H NMR (CDCl3, ppm): δ 2.70 (s, 3H), 3.09 (s, 3H), 3.18 (t, J=8.5 Hz, 2H), 3.72 (t, J=8.5 Hz, 2H), 10.09 (s, 1H). 13C NMR (CDCl3, ppm): 623.21, 24.06, 31.48, 51.19, 112.28, 112.40, 120.01, 151.18, 165.51, 166.54, 185.22; 19F NMR (CDCl3, ppm): δ−73.54 (s, 3F); HRMS (APCI+) calculated for C11H12N2O4SF3 (M+H+) 325.0470. found 325.0465.

Provenance & Evidence