Реакция #1869113

Уравнение реакции

HCl

Estra-1,3,5(10),6-tetraen-3-ol-17-one

hydrazine

potassium hydroxide

→

Estra-1,3,5(10),6-tetraen-3-ol

Растворители

water

diethylene glycol

Условия реакции

Обработка

1. 1
   workup.ADDITIONwere added
2. 2
   ЭкстракцияThe resulting suspension was extracted three times with 10 mL of ether
3. 3
   Промывкаthe combined organic extracts were washed with 10 mL of brine
4. 4
   Сушкаdried over magnesium sulfate
5. 5
   Фильтрацияfiltered through Celite
6. 6
   Концентрированиеconcentrated under reduced pressure
7. 7
   ДругоеThe crude solid was purified by preparative TLC (25% ethyl acetate/hexane on silica gel)
8. 8
   Другоеto give product homogeneous to TLC (5.9 mg, 23 μmol, 7%)

Методика

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%).

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