[C:1]1([S:7][CH2:8]P(=O)(OCC)OCC)[CH:6]=[CH:5]C=C[CH:2]=1.C([Li])CCC.CN1CCN([C:29]2[C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=3[C:33](=[O:40])[C:32]3[CH:41]=[CH:42][CH:43]=[CH:44][C:31]=3[CH:30]=2)CC1.Cl>C1COCC1.C(Cl)(Cl)Cl>[S:7]1[CH:8]=[CH:5][CH:6]=[C:1]1/[CH:2]=[C:29]1\[C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=2[C:33](=[O:40])[CH2:32][C:41]2[CH:42]=[CH:43][CH:44]=[CH:31][C:30]\1=2
To a stirred solution of 3.25 g (12.5 mmol) of diethyl phenylthiomethylphosphonate in 7.0 mL of THF at 0° C. under N2 was added 7.8 mL of a 1.6M solution of n-butyllithium dropwise via syringe. The solution was stirred at 0° C. for 45 minutes, followed by the dropwise addition of a solution of 3.04 g (10.0 mmol) of 10-(4'-methylpiperazin-1-yl)-5H-dibenzo[a,d]cyclohepten-5-one in 10.0 mL of THF via cannula. After stirring for 1 hour at 0° C., the solution was warmed to 22° C. over 45 minutes, and stored at -5° C. for 48 hours. The reaction mixture was poured into 200 mL of 5% HCl and stirred rapidly with 300 mL of CHCl3 for 1 hour. The organic layer was worked up to give 5.3 g of a yellow foam which was chromatographed on 500 g of SiO2 using CHCl3 to give 2.14 g (65%) of product as a yellow foam. A small sample was crystallized from CH3OH to give a pale yellow solid. m.p. 203.5°-205° C.
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