Water → HCID 69640848, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 571 mg (1.47 mmol) of 46 crude, 2.54 g (45.3 mmol) KOH in H2O (6 mL) and ethylene glycol (34 mL) was stirred and heated at 160° C. for 112 h without a reflux condenser to allow H2O to evaporate. The reaction mixture was poured into H2O (700 mL) and washed with Et2O (2×, 100 mL). The aqueous phase was adjusted to pH 2 with concentrated HCl and extracted with Et2O (3×, 100 mL). Combined organic extracts were washed with 10% sodium metabisulfite (50 mL), H2O (50 mL), dried over Na2SO4 and concentrated in vacuo giving 535 mg (89%, two steps) of 47 as a tan solid. Data for 47: TLC, T-3, Rf 0.575; 1H NMR (400 MHz, DMSO-d6) 60.69 (s, 3H, H-18), 3.61 (ddd, 1H, J=8.7, 8.7, 5.0 Hz, H-17α), 4.73 (d, 1H, J=5.0 Hz, 17-OH), 5.04 (s, 2H, benzylic-H), 6.67 (d, 1H, J=2.6 Hz, H-4), 6.74 (dd, 1H, J=8.7, 2.6 Hz, H-2), 7.17 (d, 1H, J=8.7 Hz, H-1), 7.31–7.42 (m, 5H, Ar—H), 12.07 (s, 1H, OH).

Provenance & Evidence