Sodium Hydroxide → HCID 86733323, compound

Participants

Reaction Steps

3α-Acetoxy-5α-pregn-9(11)-en-20-one (3 g.) was dissolved in dioxan (300 ml.) and water (75 ml.); N-bromosuccinimide (2.1 g.) was added followed by perchloric acid (60% w/v; 1.05 ml.) in water (30 ml.) and the reaction allowed to stand at room temperature under nitrogen for 5 min. The pH was adjusted to 11.7 with 2N sodium hydroxide and the reaction mixture was allowed to stand at room temperature under nitrogen for a further 15 min; the pH was adjusted to 6 with glacial acetic acid and the mixture was poured into water. The steroid was extracted with ether to give a crystalline solid (3.2 g.); crystallisation from ether-petrol followed by recrystallisation from aqueous methanol gave the title compound m.p. 133°-136°, [α]D + 105°.

Provenance & Evidence