C([C@H:5]1[C@H:10]2[C@H:11]3[C:20]([CH2:21][CH2:22][C@:8]2([CH3:9])[C:7](=[O:24])[CH2:6]1)=[C:19]1[C:14](=[CH:15][C:16](=[O:23])[CH2:17][CH2:18]1)[CH2:13][CH2:12]3)CCC.C1(SCl)C=CC=CC=1>C(Cl)Cl.C(N(CC)CC)C>[CH3:9][C@:8]12[CH2:22][CH2:21][C:20]3[C@@H:11]([CH2:12][CH2:13][C:14]4[C:19]=3[CH2:18][CH2:17][C:16](=[O:23])[CH:15]=4)[C:10]1=[CH:5][CH2:6][C:7]2=[O:24]A solution of 1.5 g of 15 α-hydroxy-4,9-estradiene-3,17-dione in 20 ml of methylene chloride and 1.2 ml of triethylamine is mixed with a solution of 0.83 g of phenylsulfenyl chloride in 5 ml of methylene chloride drop by drop at -20° C. After addition, stirring is performed for 10 minutes at -20° C., the reaction solution is then diluted with 100 ml of methylene chloride, washed, one after the other, with saturated sodium hydrogen carbonate solution and saturated ammonium chloride solution, dried with sodium sulfate and concentrated. Crystallization of the crude product from ethyl acetate/diisopropyl ether yields 1.24 g (88.2% of theory) of 4,9,14-estratriene-3,17-dione with a melting point of 143° to 144° C.
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