Hydrochloric Acid → HCID 10525398, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 784.4 mg (1.75 mmol) of 6, 5% aqueous KOH in MeOH (7 mL) was stirred and heated at 50° C. for 3 h. Reaction was cooled to rt, poured into H2O (50 mL), adjusted to pH 1 with 10% aqueous HCl, and extracted with EtOAc (3×, 100 mL). Combined organic extracts were washed with H2O (100 mL), dried over Na2SO4, and concentrated in vacuo. Purification of the residue by flash chromatography on a 2×17 cm column of silica gel using EtOH/EtOAc (10:90) gave 491.5 mg (69%) of 7 as a white foam. Data for 7: TLC, T-4, Rf0.63. 1H NMR (500 MHz, CDCl3) δ 0.86 (2, 3H, H-18), 3.94 (d, 1H, J=8.3 Hz, H-17α), 5.04 (s, 2H, benzylic), 6.73 (d, 1H, J=2.2 Hz, H-4), 6.80 (dd, 1H, J=8.7, 2.2 Hz, H-2), 7.21 (d, 1H, J=8.7 Hz, H-1), 7.32-7.45 (m, 5H, Ar—H).

Provenance & Evidence