Hydrochloric Acid → (17beta)-3-Oxoandrost-4-ene-17-carboxylic acid

HRID 1165507

Reaktionsgleichung

Reaktionsgleichung von HRID 1165507
[CH3:1][C@:2]12[CH2:19][CH2:18][C@H:17]3[C@@H:7]([CH2:8][CH2:9][C:10]4[C@:15]3([CH3:16])[CH2:14][CH2:13][C:12](=[O:20])[CH:11]=4)[C@@H:6]1[CH2:5][CH2:4][C@@H:3]2[C:21]([O:23]C)=[O:22].O.[OH-].[K+].Cl>CO>[CH3:1][C@:2]12[CH2:19][CH2:18][C@H:17]3[C@@H:7]([CH2:8][CH2:9][C:10]4[C@:15]3([CH3:16])[CH2:14][CH2:13][C:12](=[O:20])[CH:11]=4)[C@@H:6]1[CH2:5][CH2:4][C@@H:3]2[C:21]([OH:23])=[O:22]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 962Water2×HCID 14797Potassium HydroxideHCID 165014Methyl (17beta)-3-oxoandrost-4-ene-17-carboxylate

Produkt 1

HCID 99472(17beta)-3-Oxoandrost-4-ene-17-carboxylic acidAusbeute 94,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Methyl androst-4-ene-3-one-17β-carboxylate (20 g, 60 mmol) was dissolved in 700 ml of a 20:1 solution of methanol:water and potassium hydroxide (7 g) was added and the solution was refluxed under argon for 24 hours. The reaction mixture was then acidified with 5% hydrochloric acid and 250 ml water was added. After aging for 1 hour, the mixture was filtered and dried to yield 18 g (94%) of androst-4-ene-3-one-17β-carboxylic acid as a white crystalline solid.

Aufarbeitung

  1. temperaturethe solution was refluxed under argon for 24 hours
  2. additionwas added
  3. filtrationthe mixture was filtered
  4. customdried

Quellen und Nachweise

ORD-Eintrag
ord-0daa8b0b595e4355819b2370d90cb463
Quelldatensatz
uspto-grants-1990_03
Patentnummer
US04910226

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