1,2-Dimethoxyethane → Testosterone, acetate

HRID 1576165Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1576165
[CH3:1]P(=O)(OCCCC)OCCCC.C(COC)OC.C([Li])CCC.[C:25]([O:28][C@H:29]1[CH2:34][CH2:33][C@H:32]2[C@H:35]3[C@H:45]([CH2:46][CH2:47][C@:30]12[CH3:31])[C@:43]1([CH3:44])[C:38](O[C:40](=[O:48])[CH2:41][CH2:42]1)=[CH:37][CH2:36]3)(=[O:27])[CH3:26]>CCCCCC.O.O1CCCC1>[CH3:26][C:25]([O:28][C@@H:29]1[C@@:30]2([CH3:31])[CH2:47][CH2:46][C@@H:45]3[C@:43]4([CH3:44])[C:38](=[CH:1][C:40]([CH2:41][CH2:42]4)=[O:48])[CH2:37][CH2:36][C@H:35]3[C@@H:32]2[CH2:33][CH2:34]1)=[O:27]

Komponenten

8

Edukt 4

HCID 80711,2-DimethoxyethaneHCID 16994Dibutyl methylphosphonateHCID 5390371317beta-Acetoxy-4-oxa-androst-5-en-3-oneHCID 178418339Butyllithium

Produkt 1

HCID 92145Testosterone, acetate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8058HexaneLösungsmittel

Versuchsvorschrift

To a suspension of 4 g. of dibutyl methylphosphonate in 75 ml. of dry monoglyme at about -78° under nitrogen, there is added with stirring one equivalent of n-butyl lithium in hexane. After about 10 minutes, there is added one equivalent of 17β-acetoxy-4-oxa-androst-5-en-3-one in 75 ml. of dry tetrahydrofuran while maintaining the temperature at about -78°. The reaction mixture is allowed to warm to room temperature and then left to stand for about four hours. The reaction mixture is diluted with water and extracted with ether. The ether extracts are combined, washed, dried and evaporated to give testosterone acetate (17β-acetoxyandrost-4-en-3-one) which can be purified by chromatography.

Aufarbeitung

  1. additionTo a suspension of 4 g
  2. waitleft
  3. waitto stand for about four hours
  4. extractionextracted with ether
  5. washwashed
  6. customdried
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-e61a96219f5349b19110d81e6911fac4
Quelldatensatz
uspto-grants-1976_09
Patentnummer
US03979458

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