[OH:1][C:2]1[CH:19]=[CH:18][C:17]2[C:16]3[CH2:15][CH2:14][C@@:12]4([CH3:13])[C@@H:8]([CH2:9][CH2:10][C:11]4=[O:20])[C:7]=3[CH2:6][CH2:5][C:4]=2[CH:3]=1.C1(C)C=CC(S(O)(=O)=[O:28])=CC=1.N1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>O1CCCC1.O1C=CCCC1.C(OCC)(=O)C>[O:28]1[CH2:37][CH2:36][CH2:35][CH2:34][CH:33]1[O:1][C:2]1[CH:19]=[CH:18][C:17]2[C:16]3[CH2:15][CH2:14][C@@:12]4([CH3:13])[C@@H:8]([CH2:9][CH2:10][C:11]4=[O:20])[C:7]=3[CH2:6][CH2:5][C:4]=2[CH:3]=1A suspension of 2.0 g of 3-hydroxy-estra-1,3,5(10),8-tetraen-17-one in 20 ml of tetrahydrofuran and 2.0 ml of dihydropyran is stirred with 9.4 mg of para-toluenesulfonic acid for 3 hours at room temperature. Then, 0.3 ml of pyridine is added, diluted with ethyl acetate, washed with sodium bicarbonate solution as well as with saturated sodium chloride solution, dried on sodium sulfate, concentrated by evaporation in a vacuum and chromatographed on silica gel with hexane/acetone/triethylamine. 2.4 g of 3-tetrahydropyranyloxy-estra -1,3,5(10),8-tetraen-17-one is obtained as colorless crystals with a melting point of 122-125° C., [α]D22 =+0.00° (c=0.515% in pyridine).
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