(13S)-3-methoxy-13-methyl-7,11,12,16-tetrahydro-6H-cyclopenta[a]phenanthren-17-one → Estra-1,3,5(10),8-tetraen-17-one, 3-methoxy-
Reaktionsgleichung
[CH3:1][C@:2]12[CH2:10][CH2:9][C:8]3[C:11]4[CH:12]=[CH:13][C:14]([O:19][CH3:20])=[CH:15][C:16]=4[CH2:17][CH2:18][C:7]=3[C:6]1=[CH:5][CH2:4][C:3]2=[O:21]>O1CCOCC1.[Ni]>[CH3:1][C@:2]12[CH2:10][CH2:9][C:8]3[C:11]4[CH:12]=[CH:13][C:14]([O:19][CH3:20])=[CH:15][C:16]=4[CH2:17][CH2:18][C:7]=3[C@@H:6]1[CH2:5][CH2:4][C:3]2=[O:21]Komponenten
4
Edukt 1
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
Dissolve 13β-methyl-3-methoxygona-1,3,5(10),8,14-pentaen-17-one (1 g) in dioxan (33 cc). To the solution add Raney nickel catalyst (ca. 0.5 g) which has been prepared by the method of Pavlic and Adkins, J. Amer. Chem. Soc., 1946, 68, 1471 and allow to stand for 24 hours. Hydrogenate at room temperature and pressure until the theoretical amount of hydrogen (92 cc) for saturation of one ethylenic linkage has been absorbed. Towards the end of this period (5 hours) the rate of hydrogenation drops markedly. Evaporate the solvent after removal of catalyst to obtain a gum which readily crystallizes. Recrystallize once from ethanol to obtain the crude title product (0.69 g), m.p. 110°-120°; ultraviolet absorption peak at 278 mμ (ε14,700).