6,6-Dichloro-2-(5-methoxyhept-1-yl)bicyclo[3.3.0]octan-7-one → Cioteronel

Reaktionsgleichung

Cl[C:2]1(Cl)[C:9](=[O:10])[CH2:8][CH:7]2[CH:3]1[CH2:4][CH2:5][CH:6]2[CH2:11][CH2:12][CH2:13][CH2:14][CH:15]([O:18][CH3:19])[CH2:16][CH3:17]>[Zn].[Cl-].[Cl-].[Zn+2].C(O)(=O)C>[CH3:19][O:18][CH:15]([CH2:16][CH3:17])[CH2:14][CH2:13][CH2:12][CH2:11][CH:6]1[CH2:5][CH2:4][CH:3]2[CH:7]1[CH2:8][C:9](=[O:10])[CH2:2]2

Komponenten

Versuchsvorschrift

6,6-dichloro-2-(5-methoxyhept-1-yl)bicyclo[3.3.0]octan-7-one {1,1-dichlorohexahydro-4-(5-methoxyheptyl)-2(lH)-pentalenone} or the isomer (45.9 g) are added to a single-neck 100 ml, round-bottom flask equipped with a condenser. The solution is stirred by a magnetic stirrer and powdered zinc metal (92 g) and glacial acetic acid (312 ml) are added and the solution heated under reflux for one hour, during which time white ZnCl2 precipitates out of solution. The solution is filtered, washed with sodium hydrogen carbonate and extracted three times with ether. The ether extracts are combined and dried over anhydrous sodium sulfate. The resulting yellow oil is chromatographed with silica gel and eluted with 3:1 hexane:ether. The fractions are combined, yielding 2-(5-methoxyhept-1-yl)-bicyclo[3.3.0]octan7-one {hexahydro-4-(5-methoxyheptyl)-2(1H)-pentalenone} as a clear, colorless oil. B.