Experimental
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Part 1, Ketalization of Adrenosterone:
A solution of 12.8g of adesterone (42.6mmol) dissolved in
530mL of toluene was prepared. To this was added 70mL
of ethylene glycol and 0.81g of hydrous p-TsOH (4.26mmol).
The reaction vessel was then put into an oil bath preheated
to 140°C and let to stir vigorously. This reaction was let to
commence for 6 hours before being removed from the bath
and let cool down to room temperature. The solution being
made of different parts, the solution was then let set and
the organic layer was separated from the ethylene glycol.
The reaction was quenched with 100mL saturated aqueous
NaHCO3. The aqueous portion was extracted with ethyl
acetate (3X100mL). The organic layer collected from
this extraction was combined with the organic layer
from the previous extraction, then washed with saturated
aqueous NaCl (150mL), then dried with MgSO4.
The resulting product was then
recrystallized by boiling with a 10:1 mixture of ethyl ether and ethyl acetate (combined 450mL) This was then cooled to 4°C and furnished with known compound SI-0 after three cycles.
Figure 1: Part 1
Part 2, Solid State Photolysis of Crystal Suspension:
Crystals of the previous product (2.00g, 5.15mmol) and 1g of sodium dodecyl sulfate (1.0g) were put into a photoreaction chamber with a quartz immersion well. Degassed water (1.0L purged with argon) was added followed by irradiation using a 450W mercury Hanovia lamp through a vycor filter for 120 hours. The resulting mixture was poured into a separatory funnel and extracted with ethyl acetate (3X150mL). The organic layer was then washed with 250mL of brine, dried over MgSO4, then filtered through a pad of silica to remove any remaining sodium dodecyl sulfate. This was then concentrated in vacuo, then purified with column chromatography.
Figure 2: Part 2
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