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

HRID 582855Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 582855
[CH3:1][C@:2]12[CH2:18][CH2:17][C@H:16]3[C@@H:7]([CH:8]=[CH:9][C:10]4[CH:11]=[C:12]([OH:19])[CH:13]=[CH:14][C:15]=43)[C@@H:6]1[CH2:5][CH2:4][C:3]2=O.NN.[OH-].[K+].Cl>C(O)COCCO.O>[CH3:1][C@:2]12[CH2:18][CH2:17][C@H:16]3[C@@H:7]([CH:8]=[CH:9][C:10]4[CH:11]=[C:12]([OH:19])[CH:13]=[CH:14][C:15]=43)[C@@H:6]1[CH2:5][CH2:4][CH2:3]2

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 9321HydrazineHCID 14797Potassium HydroxideHCID 1022253-Hydroxyestra-1,3,5(10),6-tetraen-17-one

Produkt 1

HCID 15480542Estra-1,3,5(10),6-tetraen-3-ol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8117Diethylene GlycolLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

  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%)

Quellen und Nachweise

ORD-Eintrag
ord-48d8f9811ee9410baa15c8f43d474ba4
Quelldatensatz
uspto-grants-1999_07
Patentnummer
US05925774

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