Acetic Acid → Desogestrel

Participants

Reaction Steps

100 g (0.35 moles) of 13-ethyl-11-methylen-gon-4-ene (compound XVIII) were dissolved in anhydrous dimethylsulfoxide (3 liters) under stirring at room temperature. 430 g of lithium acetylide complexed with ethylendiamine were added to the so obtained solution and the stirring at room temperature was carried on for 21 hours. After this period the reaction was spilled in water cooled at a temperature of 2° C. (3 liters) then a 10% aqueous solution of acetic acid was added (7 liters) and the aqueous phase was extracted with dichloromethane (3×2 liters). The organic extracts were subsequently washed with a saturated solution of sodium bicarbonate (2 liters) and then with a saturated solution of sodium chloride. The organic phase was then dehydrated on sodium sulfate, filtered and evaporated to dryness to give 96.24 g (0.31 moles; yields 89%) of Desogestrel.

Provenance & Evidence