Reaktion #456880

Reaktionsgleichung

water

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

hydrazine

potassium hydroxide

→

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

Lösungsmittel

HCl

diethylene glycol

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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 IN 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%).

Quelle