Acetone → HCID 66931861, compound

Participants

Reaction Conditions

Reaction Steps

Sodium borohydride (MW=37.8; 18.9 g; 500 mmol) dissolved in 0.5 N sodium hydroxide (100 ml) was introduced over about 5 min at around 2° C. into a suspension of 3,3-ethylenedioxyestra-5(10),9(11)-diene-17-one (MW=314.4; 100 g; 318 mmol) in methanol (1 liter). The medium was stirred for 2 h at around 2° C. and then acetone (100 ml) was introduced over about 15 min at around 5° C. The medium was stirred for 1 h, and poured at around 20° C. into the stirred mixture of water (2 liters), sodium chloride (500 g) and ethyl acetate (400 ml). The medium was separated by decantation and the aqueous phase was re-extracted with ethyl acetate. The combined organic phases were washed with water, dried over sodium sulfate and concentrated at atmospheric pressure at 500 ml. The distillation is continued while the volume is kept constant by gradual introduction of 1,2-dimethoxyethane (DME). The temperature at the end of the exchange is 83° C. The solution was used as it is in the next step, but a dry extract gave the expected product (resin). C20H28O3; MW=316.4.

Provenance & Evidence