反应详情

Estra-1,3,5(10),6-tetraen-3-ol-17-one (91.1 mg, 0.339 mmol), hydrazine (54 μL, 1.7 mmol), and potassium hydroxide (0.06 g) in 1.8 mL of diethylene glycol were heated in a 200° C. bath under argon for 2 h. After cooling to RT 10 mL of water were added and the solution was acidified to pH≈2 with 1N HCl. The resulting suspension was extracted three times with 10 mL of ether and the combined organic extracts were washed with 10 mL of brine, dried over magnesium sulfate, filtered through Celite, and concentrated under reduced pressure. The crude solid was purified by preparative TLC (25% ethyl acetate/hexane on silica gel) to give product homogeneous to TLC (5.9 mg, 23 μmol, 7%).

1. additionwere added
2. extractionThe resulting suspension was extracted three times with 10 mL of ether
3. washthe combined organic extracts were washed with 10 mL of brine
4. dry with materialdried over magnesium sulfate
5. filtrationfiltered through Celite
6. concentrationconcentrated under reduced pressure
7. customThe crude solid was purified by preparative TLC (25% ethyl acetate/hexane on silica gel)
8. customto give product homogeneous to TLC (5.9 mg, 23 μmol, 7%)