ChemicalBook CAS DataBase List 7-Keto-dehydroepiandrosterone

7-Keto-dehydroepiandrosterone synthesis

7synthesis methods

Product Name:7-Keto-dehydroepiandrosterone
CAS Number:566-19-8
Molecular formula:C19H26O3
Molecular Weight:302.41

53-43-0 Synthesis

53-43-0
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$27.00/10g

566-19-8
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$39.00/5mg

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]