ChemicalBook CAS DataBase List cholesta-1,4,6-trien-3-one

cholesta-1,4,6-trien-3-one synthesis

11synthesis methods

Product Name:cholesta-1,4,6-trien-3-one
CAS Number:3464-60-6
Molecular formula:C27H40O
Molecular Weight:380.61

57-88-5 Synthesis

57-88-5
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3464-60-6
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Yield:3464-60-6 91%

Reaction Conditions:

with allyl diethyl phosphate;palladium 10% on activated carbon;sodium carbonate in N,N-dimethyl-formamide at 20; for 20 h;Inert atmosphere;Reflux;Green chemistry;

Steps:

General procedure for the palladium catalyzed dehydrogenation of sterols

General procedure: To a solution of ADP (54.95 g, 283.2 mmol) in anhydrous DMF 200 mL was added 10% Pd/C (1.57 g) at room temperature and stirred under nitrogen atmosphere for 30 min. Sodium carbonate (40 g, 377.6 mmol) and 17,17-ethylenedioxydehydroepiandrosterone 1 (15.7 g, 47.2 mmol) were added. The mixture was vigorously refluxed for 16 h. After cooling, the mixture was filtered to recover the Pd/C. Distilled water (200 mL) was added to the filtrate and the mixture was extracted with EtOAc (100 mL 3). The combined organic layers were washed with brine, dried over Na2SO4, and concentrated. Recrystallization from methanol afforded product 2 as light yellow crystals (13.8 g, 89%).

References:

Yin, Yi-Zhen;Liu, Chao;Tang, Long-Qian;Liu, Zhao-Peng [Steroids,2012,vol. 77,# 13,p. 1419 - 1422]