Hydrochloric Acid → (3S,8S,9S,10R,13S,14S,16S,17R)-17-[(1R,5R)-6-hydroxy-1,5-dimethyl-hexyl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,16-diol

Participants

Reaction Steps

To a 5-liter flask were sequentially added diosgenin (40 grams, 0.0965 moles, zinc dust (900 grams, -325 mesh size) and 2 liters of absolute ethanol. The suspension was then brought to reflux and 800 ml of concentrated HCl was added dropwise over a period of 2.5 hours. The reaction was refluxed for an additional 30 minutes then immediately filtered while hot, under gravity, over Whatman no. 2 filter paper to remove the zinc particles. Two liters of water was then added to the filtrate and a white precipitate formed. The mixture was cooled at room temperature and the precipitate was collected by suction filtration (Whatman no. 2 paper) and washed three times with water, then air dried to afford 35 grams (85% yield) of compound (2).

Provenance & Evidence