Sodium Carbonate → 19-Hydroxy-17beta(1-oxopropoxy)androst-4-en-3-one

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[O:1]=[C:2]([O:5][C@H:6]1[CH2:11][CH2:10][C@H:9]2[C@H:12]3[C@H:27]([CH2:28][CH2:29][C@:7]12[CH3:8])[C@:20]1([CH2:21][O:22]C(=O)CC)[C:15](=[CH:16][C:17](=[O:30])[CH2:18][CH2:19]1)[CH2:14][CH2:13]3)[CH2:3][CH3:4].C(=O)([O-])[O-].[Na+].[Na+]>CO.O>[OH:22][CH2:21][C@@:20]12[C@@H:27]3[C@H:12]([C@H:9]4[C@@:7]([CH2:29][CH2:28]3)([CH3:8])[C@@H:6]([O:5][C:2](=[O:1])[CH2:3][CH3:4])[CH2:11][CH2:10]4)[CH2:13][CH2:14][C:15]1=[CH:16][C:17](=[O:30])[CH2:18][CH2:19]2

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실험 절차

A solution of 11 g of 17β,19-bis(1-oxopropoxy)androst-4-en-3-one in 2 liters of methanol is treated with 2.5 g of sodium carbonate in 250 ml of water and refluxed for one hour after which the reaction mixture is poured into 10 liters of water, and the solid collected by filtration. The solid is dissolved in methylene chloride, dried over magnesium sulfate, filtered and the solvent removed. The residue is crystallized from acetone-hexane yielding 6 g of 19-hydroxy-17β(1-oxopropoxy)androst-4-en-3-one. M.P. 160°-162° C.