Hydrochloric Acid → 4-Methyl-4-androsten-3,17-dione

HRID 1200173

Reaktionsgleichung

Reaktionsgleichung von HRID 1200173
[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:3]2=[O:21].[CH3:22]C(C)([O-])C.[K+].CCl.Cl>C(O)(C)(C)C.O>[CH3:22][C:11]1[C:12](=[O:20])[CH2:13][CH2:14][C@@:15]2([CH3:16])[C:10]=1[CH2:9][CH2:8][C@@H:7]1[C@@H:17]2[CH2:18][CH2:19][C@@:2]2([CH3:1])[C@H:6]1[CH2:5][CH2:4][C:3]2=[O:21]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 6128AndrostenedioneHCID 6327Methyl ChlorideHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 147309424-Methyl-4-androsten-3,17-dione

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6386tert-ButanolLösungsmittel3×

Versuchsvorschrift

A solution of androst-4-ene-3,17-dione in t-butanol was heated to boiling and added to a boiling solution of potassium t-butoxide in t-butanol. Methyl chloride in t-butanol was added slowly. The solution was cooled, acidified with concentrated hydrochloric acid, and diluted with water. The excess t-butanol was removed under vacuum and the aqueous layer extracted with ethylacetate. The combined extracts were washed with water, dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel and eluted with hexane/ethylacetate. The eluant was evaporated and the residue crystallized from ether to yield 4-methylandrost-4-ene-3,17-dione; I.R. (KBr): 1735 (17-oxo), 1660 (3-oxo), 1620 cm-1 (Δ4).

Aufarbeitung

  1. temperatureThe solution was cooled
  2. customThe excess t-butanol was removed under vacuum
  3. extractionthe aqueous layer extracted with ethylacetate
  4. washThe combined extracts were washed with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was chromatographed on silica gel
  8. washeluted with hexane/ethylacetate
  9. customThe eluant was evaporated
  10. customthe residue crystallized from ether

Quellen und Nachweise

ORD-Eintrag
ord-ac90653361494d16bb9441bd53d48655
Quelldatensatz
uspto-grants-1990_02
Patentnummer
US04904650

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