Estrone → Oestrone Acetate

Beteiligte Stoffe

Reaktionsschritte

A mixture of oestrone (10 g, 36.82 mmol), acetic anhydride (17.5 ml) and pyridine (75 ml) was heated under reflux for 2 h. The cooled reaction mixture was concentrated in vacuo and then quenched with ice-water. The precipitate that formed was filtered off, washed with water, dried, and recrystallised from aqueous ethanol (95%) to give 1 as white crystals (11.2 g, 97%); mp 115-118° C.; TLC (chloroform/acetone, 8:1): Rf 83; νmax (KBr) 1770, 1720 (C═O) cm−1; δH (400 MHz, CDCl3) 0.91 (3H, S, C-18-CH3), 1.42-2.19 (11H, m), 2.29 (3H, s, CH3CO), 2.38-2.54 (2H, m), 2.9 (2H, t, J=4.43 Hz, C-6-CH2), 6.81 (1H, d, JC-2-H, C-4-H=2.14 Hz, C-4-H), 6.86 (1H, dd, JC-4-H, C-2-H=2.44 Hz and JC-1-H, C-2-H=8.54 Hz, C-2-H) and 7.28 (1H, d, JC-2-H, C-1-H=8.24 Hz, C-1-H); MS m/z (FAB+) 466.2 [10, (M+H+NBA)+], 313.2 [65, (M+H)+], 270.2 [100, (M+H−CH3CO)+]; MS m/z (FAB−) 269.2 [100, (M−CH3CO)−]. Found C, 76.9; H, 7.83 C20H24O3 requires C, 76.89; H, 7.74%.

Herkunft & Nachweise