C([Li])CCC.[CH2:6]([NH:8][C:9]1[C:10]2[C:15]([C:16]3[C:17]([O:25][CH3:26])=[C:18]([O:23][CH3:24])[CH:19]=[CH:20][C:21]=3[CH:22]=1)=[CH:14][C:13]([CH3:27])=[CH:12][CH:11]=2)[CH3:7].S([O-])([O-])(=O)=O.[Na+].[Na+].[C:35](=O)=[O:36]>CCCCCC.O1CCCC1>[CH2:6]([N:8]1[C:9]2[CH:22]=[C:21]3[CH:20]=[CH:19][C:18]([O:23][CH3:24])=[C:17]([O:25][CH3:26])[C:16]3=[C:15]3[CH:14]=[C:13]([CH3:27])[CH:12]=[C:11]([C:10]=23)[C:35]1=[O:36])[CH3:7]
661.4 ml (1.084M) of a 15% solution of n-butyl-lithium in hexane are added at 0°, over a period of 20 minutes and under a nitrogen atmosphere, to a solution of 97 g (0.328M) of 9-ethylamino-3,4-dimethoxy-6-methyl-phenanthrene in 1000 ml anhydrous tetrahydrofuran; the reaction mixture becomes dark red. After stirring for 30 minutes at 0°, the mixture is transferred in portions with a teflon tube with nitrogen pressure at -50° onto a mixture of 500 g sodium sulfate and 500 g dry ice in 1500 ml tetrahydrofuran. After the temperature of the mixture has reached room temperature, the mixture is poured onto water/ice, extracted three times with methylene chloride. The combined organic phases are dried over sodium sulfate and evaporated to give the title compound. M.pt. 158°-160° (decomp.) after crystallisation from ether/petroleum ether.
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