Reaktion #2311228

Reaktionsgleichung

ethanol

hydrochloric acid

DIBAH

3-methoxy-8β-methyl-estra-1,3,5(10)-trien-17β-ol

→

colorless crystals

Ausbeute 99.2%

8β-methyl-estra-1,3,5(10)-triene-3,17β-diol

Ausbeute 99.2%

Lösungsmittel

ethanol water

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was slowly refluxed
2. 2
   TemperaturThen, it was cooled again to 0° C.
3. 3
   Extraktionextracted several times with ethyl acetate
4. 4
   WaschenThe collected organic phases were washed neutral with water
5. 5
   Trocknendried with magnesium sulfate
6. 6
   Sonstigeevaporated to the dry state in a vacuum

Vorschrift

74 mg of 3-methoxy-8β-methyl-estra-1,3,5(10)-trien-17β-ol was dissolved in 3 ml of anhydrous toluene, cooled to 0° C. and mixed carefully under argon with 0.6 ml of DIBAH. The reaction mixture was slowly refluxed, and it was kept at this temperature for 3.5 hours. Then, it was cooled again to 0° C., the solution was mixed in succession with 2 ml of ethanol, 2 ml of ethanol-water mixture (v/v=1/1) and 2 ml of semi-concentrated hydrochloric acid and extracted several times with ethyl acetate. The collected organic phases were washed neutral with water, dried with magnesium sulfate and evaporated to the dry state in a vacuum. 70 mg (99%) of colorless crystals with a melting point of 168-170° C. was obtained.

Quelle