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

HRID 369698Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 369698
[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+].O>C(O)COCCO.Cl>[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 962WaterHCID 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 313Hydrochloric AcidLösungsmittelHCID 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 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%).

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-83e78d17d7a74febab39cfe141cc4905
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06140316

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