Reaktion #362864

Reaktionsgleichung

17-methylenestra-1,3,5(10)-trien-3-ol

17-Methylenestra-1,3,5(10)-trien-3-ol

pyridine

acetic anhydride

→

17-Methylenestra-1,3,5( 10)-trien-3-yl acetate

Lösungsmittel

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   WaschenThe mixture was washed with three 100 mL portions of 1 N hydrochloric acid+100 mL of saturated sodium bicarbonate+100 mL of saturated copper sulfate+100 mL of brine
2. 2
   Trocknendried over magnesium sulfate
3. 3
   Filtrationfiltered through diatomaceous earth
4. 4
   WaschenThe residue was washed with 25 mL of ethyl acetate
5. 5
   Einengenthe combined filtrates were concentrated under reduced pressure
6. 6
   SonstigeRecrystallization from aqueous ethanol
7. 7
   Sonstigegave lustrous white platelets (5.84 g, 18.8 mmol), m.p. 77-79° C.

Vorschrift

A solution of 17-methylenestra-1,3,5(10)-trien-3-ol (10, 5.84 g, 21.8 mmol) in anh. pyridine (32 mL, 0.40 mol) and acetic anhydride (9.7 mL, 0.10 mol) was stirred 24, after which ethyl acetate (250 mL) was added. See FIG. 17. The mixture was washed with three 100 mL portions of 1 N hydrochloric acid+100 mL of saturated sodium bicarbonate+100 mL of saturated copper sulfate+100 mL of brine, dried over magnesium sulfate, and filtered through diatomaceous earth. The residue was washed with 25 mL of ethyl acetate and the combined filtrates were concentrated under reduced pressure. Recrystallization from aqueous ethanol gave lustrous white platelets (5.84 g, 18.8 mmol), m.p. 77-79° C.

Quelle