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ChemicalBook CAS DataBase List 7-Keto-dehydroepiandrosterone
566-19-8

7-Keto-dehydroepiandrosterone synthesis

7synthesis methods
-

Yield:566-19-8 81.1%

Reaction Conditions:

with tert.-butylhydroperoxide;N-hydroxyphthalimide;cobalt(II) acetate in acetone at 20; for 5 h;regioselective reaction;

Steps:

2.1. General procedure for allylic oxidation of the Δ5-steroidal substrates

General procedure: In a typical experiment, to a solution of 25-hydroxycholesterylacetate (0.428 g, 1 mmol) in acetone (10 mL), NHPI (0.0163 g,0.1 mmol), Co(OAc)2 (0.002 g, 0.01 mmol) and TBHP (0.515 g,4 mmol) were added. After 12 h under magnetic stirring at ambient temperature (TLC monitoring), the solution was poured into sodium sulfite solution (10% aq.) and extracted with dichloromethane. The extract was washed with an aq. saturated solution of NaHCO3, water, dried over anhydrous sodium sulfate, and evaporated. The final products were isolated using column chromatography (absorbent: silica gel, mobile phase: n-hexane/EtOAc (8:1, v/v)).

References:

Zhao, Qian;Qian, Chao;Chen, Xin-Zhi [Steroids,2015,vol. 94,p. 1 - 6]

7-Keto-dehydroepiandrosterone Related Search:

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