Sodium Sulfide → HCID 58191367, compound

Participants

Reaction Steps

Compound 371 (18.7 g, 65 mmol) suspended in anhydrous methanol (50 ml) was added slowly to a solution of dry sodium sulfide (10.0 g, 129 mmol) in methanol (50 ml) while keeping the internal temperature below 40° C. The solution was stirred for 1 h at room temperature then quenched by pouring into a rapidly stirred mixture of ice (350 ml) and 2M HCl (200 ml). The mixture was extracted with dichloromethane (3×250 ml) and the combined extracts dried with brine (100 ml) then sodium sulfate and concentrated under reduced pressure. Flash chromatography (ISCO system, silica, 0-30% ethyl acetate in hexane) provided 372 (12.2 g, 66%) as a crystalline solid.

Provenance & Evidence