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Acetylene → HCID 86747115, Verbindung

HRID 2254622
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2254622
C#C.[CH2:3]([Li])[CH2:4]CC.C(O[C@@H:12]1[C@H:17]2[C@H:18]3[C@H:28]([CH2:29][CH2:30][C@:15]2([CH3:16])[C:14](=[O:33])[CH2:13]1)[C@:26]1([CH3:27])[C:21]([CH:22]=[C:23]([O:31]C)[CH2:24][CH2:25]1)=[CH:20][CH2:19]3)(=O)C.[Cl-].[NH4+]>O1CCCC1.C(OCC)(=O)C>[C:3]([C@:14]1([OH:33])[CH:13]=[CH:12][C@H:17]2[C@H:18]3[C@H:28]([CH2:29][CH2:30][C@:15]12[CH3:16])[C@:26]1([CH3:27])[C:21](=[CH:22][C:23](=[O:31])[CH2:24][CH2:25]1)[CH2:20][CH2:19]3)#[CH:4]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 6326AcetyleneHCID 25517Ammonium ChlorideHCID 54571005(15alpha)-15-(Acetyloxy)-3-methoxyandrosta-3,5-dien-17-oneHCID 178418339Butyllithium

Produkt 1

HCID 86747115HCID 86747115, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028
Tetrahydrofuran
Lösungsmittel
2×
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Acetylene is introduced at 0° C. for 45 minutes into 200 ml of butyllithium solution (1.6 molar in hexane) in 600 ml of tetrahydrofuran. Then, 20.0 g of 15α-acetoxy-3-methoxyandrosta-3,5-dien-17-one in 400 ml of tetrahydrofuran is added thereto. After 2 hours, the mixture is gently combined with saturated ammonium chloride solution, diluted with ethyl acetate, washed with water, dried, and concentrated under vacuum. At room temperature, 14 ml of concentrated hydrochloric acid is added dropwise to the crude product in 400 ml of methanol and 50 ml of water. After 1.5 hours, the reaction mixture is stirred into ice/water. The thus-precipitated product is suctioned off, washed with water, dissolved in ethyl acetate, dried, and concentrated under vacuum. The crude product is chromatographed on silica gel with a hexane-ethyl acetate gradient, thus obtaining 9.5 g of 17α-ethynyl-17β-hydroxyandrosta-4,15-diene-3-one, mp 206.4° C. (from acetone/hexane).

Aufarbeitung

  1. washwashed with water
  2. customdried
  3. concentrationconcentrated under vacuum
  4. additionAt room temperature, 14 ml of concentrated hydrochloric acid is added dropwise to the crude product in 400 ml of methanol and 50 ml of water
  5. waitAfter 1.5 hours
  6. washwashed with water
  7. dissolutiondissolved in ethyl acetate
  8. customdried
  9. concentrationconcentrated under vacuum
  10. customThe crude product is chromatographed on silica gel with a hexane-ethyl acetate gradient

Quellen und Nachweise

ORD-Eintrag
ord-70147dd731e4422bb19cb85ab011bf00
Quelldatensatz
uspto-grants-1993_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05236912

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