C(OP([CH:9]([F:11])[F:10])(=O)OCC)C.C([Li])(C)(C)C.[OH:17][C:18]1[CH:35]=[CH:34][C:33]2[C@:32]3([CH:36]=O)[C@H:23]([C@H:24]4[C@@:28]([CH2:30][CH2:31]3)([CH3:29])[CH2:27][C@H:26]([OH:38])[CH2:25]4)[CH2:22][CH2:21][C:20]=2[CH:19]=1.[Cl-].[NH4+]>C(COC)OC.CCCCC>[F:11][C:9]([F:10])=[CH:36][C@:32]12[CH2:31][CH2:30][C@@:28]3([CH3:29])[C@@H:24]([CH2:25][C@@H:26]([OH:38])[CH2:27]3)[C@@H:23]1[CH2:22][CH2:21][C:20]1[CH:19]=[C:18]([OH:17])[CH:35]=[CH:34][C:33]2=11.5 ml of dimethoxyethane (molecular sieve), 0.3 ml of pentane and 0.13 ml (0.77 mmol) of diethyl(difluoromethyl)-phosphonate are introduced into a reaction flask that was rendered inert, and cooled to about −75° C. After 0.72 ml (1.07 mmol) of tert-butyllithium (1.5 M in pentane) is added and after 30 minutes of reaction time, 0.14 g (0.31 mmol) of 3,16α-dihydroxy-estra-1,3,5(10)-triene-9-carbaldehyde, dissolved in a mixture of 1.5 ml of dimethoxyethane/0.3 ml of pentane, is added to the reaction solution. The reaction solution is refluxed until the reaction is completed. After being added into cooled ammonium chloride solution, it is extracted with ethyl acetate. The organic phase is concentrated by evaporation under vacuum, the residue is taken up in 5 ml of methanol and mixed with 0.5 ml of dilute hydrochloric acid (1/1). Ethyl acetate is added to the reaction solution, the organic phase is washed with sodium bicarbonate solution and concentrated by evaporation under vacuum. The crude product that is obtanied is purified by column chromatography on silica gel (cyclohexane/ethyl acetate, 2/1).
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