Water → HCID 67368697, compound

Reaction equation

C(N(CC)CC)C.C(O[C@@H:12]1[C@H:18]2[C@H:19]3[C@H:28]([CH2:29][CH2:30][C@:15]2([CH2:16][CH3:17])[C:14](=[O:33])[CH2:13]1)[C@@H:27]1[C:22](=[CH:23][C:24](=[O:31])[CH2:25][CH2:26]1)[CH:21]([OH:32])[CH2:20]3)(=O)C.O>CCO>[OH:32][CH:21]1[C:22]2[C@H:27]([CH2:26][CH2:25][C:24](=[O:31])[CH:23]=2)[C@@H:28]2[C@H:19]([C@H:18]3[C@@:15]([CH2:30][CH2:29]2)([CH2:16][CH3:17])[C:14](=[O:33])[CH:13]=[CH:12]3)[CH2:20]1

Participants

Procedure

Triethylamine (0.5 ml, 3.6 mmol) was added to a suspension of 15α-acetoxy-6-hydroxy-18-methyl-estr-4-en-3,17-dione (0.5 g, 1.4 mmol) in EtOH (3 ml). The mixture was heated under reflux for 2 h, cooled to room temperature and then water (30 ml) was added. The mixture was extracted with ethyl acetate (30 ml), the organic layer was washed with water (50 ml), dried and the solvent removed. The crude product was purified by flash chromatography on silica gel eluting with diisopropyl ether/ethyl acetate (7/3) to afford pure 6-hydroxy-18-methyl-estra-4,15-dien-3,17-dione (0.14 g, yield: 34%) as an oil.