Sodium Bicarbonate → HCID 10622632, compound

Participants

Reaction Steps

A solution of 183 mg (0.397 mmol) of 4 in THF (1.5 mL) with 4 drops of 10% aqueous HCl and 2 drops of H2O was stirred at rt for 6 h. Reaction was poured into saturated aqueous NaHCO3 (100 mL) and extracted with CH2Cl2 (3×, 75 mL). Combined organic extracts were dried over Na2SO4 and concentrated in vacuo. Purification of the residue by repeated (3×) flash chromatography on a 2×15 cm column of silica gel using hexanes/acetone (6:1) as eluent gave 96.9 mg (56%) of 5 as a white solid. Data for 5: TLC, T-3, Rf0.22. 1H NMR (500 MHz, CDCl3) δ 0.91 (s, 3H, H-18), 2.10 (s, 3H, OAc), 4.86 (d, 1H, J=8.1 Hz, H-17), 5.04 (s, 2H, benzylic), 6.73 (d, 1H, J=2.7 Hz, H-4), 6.79 (dd, 1H, J=8.5, 2.7 Hz, H-2), 7.19 (d, 1H, J=8.5 Hz, H-1), 7.31-7.44 (m, 5H, Ar—H), 9.83 (d, 1H, J=3.1 Hz, O═CH); HRMS (ES) calcd for C28H32O4Na (M+Na+) m/e 455.2198, found m/e 455.2205.

Provenance & Evidence