Potassium Carbonate → 1-Acetoxy-16alpha-bromo-3-methoxyestra-1,3,5(10)-trien-17-one
Reaction equation
[Br:1]Br.[C:3]([O:6][C:7]1[C:24]2[C@@H:23]3[C@H:14]([C@H:15]4[C@@:19]([CH2:21][CH2:22]3)([CH3:20])[C:18]([O:25]C(=O)C)=[CH:17][CH2:16]4)[CH2:13][CH2:12][C:11]=2[CH:10]=[C:9]([O:29][CH3:30])[CH:8]=1)(=[O:5])[CH3:4].C(=O)([O-])[O-].[K+].[K+].OS([O-])=O.[Na+]>C(Cl)(Cl)(Cl)Cl.O>[C:3]([O:6][C:7]1[C:24]2[C@@H:23]3[C@H:14]([C@H:15]4[C@@:19]([CH2:21][CH2:22]3)([CH3:20])[C:18](=[O:25])[C@H:17]([Br:1])[CH2:16]4)[CH2:13][CH2:12][C:11]=2[CH:10]=[C:9]([O:29][CH3:30])[CH:8]=1)(=[O:5])[CH3:4]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of Br2 (0.4 g, 2.5 mM) in 10 ml of carbon tetrachloride is added over a period of 5 min to a suspension of 1,17-diacetoxy-3-methoxyestra-1,3,5(10),16-tetraene (0.95 g, 2.5 mM), potassium carbonate (0.53 g) and 40 ml of carbon tetrachloride at 0°. After an additional 5 min the colorless suspension is added to a solution of NaHSO3 (1 g) in 75 ml of H2O. The layers are separated and the aqueous layer is extracted with 3 × 25 ml of chloroform, the organic layers are combined and evaporated in vacuo after drying with MgSO4. Trituration of the residue with a small amount of methanol gives 1-acetoxy-16α-bromo-3-methoxyestra-1,3,5(10)-trien-17-one, yield 0.94 g (90%); m.p. 188°-190° (methanol).
Workup
- customThe layers are separated
- extractionthe aqueous layer is extracted with 3 × 25 ml of chloroform
- customevaporated in vacuo
- dry with materialafter drying with MgSO4
Sources & evidence
- ORD record
- ord-ea879f1799b6422cb9d90b197e705256
- Source dataset
- uspto-grants-1978_06
- Patent number
- US04096253
Reaction notes
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