CS(Cl)(=O)=O.O[C@@H:7]1[C@H:13]2[C@H:14]3[C@H:23]([CH2:24][CH2:25][C@:10]2([CH2:11][CH3:12])[C:9](=[O:27])[CH2:8]1)[C@@H:22]1[C:17](=[CH:18][C:19](=[O:26])[CH2:20][CH2:21]1)[CH2:16][CH2:15]3.CN(C)C=O.C([O-])(=O)C.[Na+]>N1C=CC=CC=1>[CH3:12][CH2:11][C@:10]12[CH2:25][CH2:24][C@H:23]3[C@@H:14]([CH2:15][CH2:16][C:17]4[C@@H:22]3[CH2:21][CH2:20][C:19](=[O:26])[CH:18]=4)[C@@H:13]1[CH:7]=[CH:8][C:9]2=[O:27]At 0° C., 77.5 ml of methanesulfonyl chloride is added dropwise within 10 minutes to 250 g of 15α-hydroxy-18-methyl-4-estrene-3,17-dione in 704 ml of pyridine. After 3.5 hours, 350 ml of dimethylformamide and 283 g of anhydrous sodium acetate are added, the mixture is stirred under argon for 20 hours at room temperature, and the reaction mixture is introduced into ice water. The thus-precipitated product is suctioned off, washed with water, and dried under vacuum. For purposes of purification, the crude product (212 g) is treated with 21 g of active carbon in 1,500 ml of ethyl acetate and 0.4 ml of pyridine. After concentrating the solution to 420 ml, 188 g of 18-methyl-4,15-estradiene-3,17-dione is crystallized at 0° C. Melting point 156.9° C. (from acetone/hexane).
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