Ammonia → Gon-4-en-3-one, 13-ethyl-17-hydroxy-, (17beta)-(+-)-

Add 13β-ethyl-3-methoxy-gona-1,3,5(10)-trien-17β-ol (0.5 g.) in 100 ml. of tetrahydrofuran to 150 ml. of liquid ammonia, followed by 0.5 g. of lithium foil, and stir the mixture for 10 minutes. Add ethanol (6 ml.) and tetrahydrofuran (10 ml.) over a period of 20 minutes. After disappearance of the blue color add water, extract the mixture well with ether and evaporate the washed and dried ether extract. Dissolve the crystalline residue in 50 ml. of methanol and reflux for 30 minutes with 30 ml. of 3N HCL. Remove most of the methanol under reduced pressure, and extract the residue with ether. Chromatograph the ether extract on alumina. Use benzene-ether (1:1) to elute 13-β-ethyl-17β-hydroxy-gon-4-en-3-one; m.p. 152°-55° C.

1. extractionextract the mixture well with ether
2. customevaporate the
3. washwashed
4. extractiondried ether extract
5. dissolutionDissolve the crystalline residue in 50 ml
6. temperatureof methanol and reflux for 30 minutes with 30 ml
7. customRemove most of the methanol under reduced pressure
8. extractionextract the residue with ether
9. extractionChromatograph the ether extract on alumina
10. washto elute 13-β-ethyl-17β-hydroxy-gon-4-en-3-one

ORD-Eintrag

ord-6727c76ff08c4185bcd15a7d11b6cf86

Quelldatensatz

uspto-grants-1976_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US03959322