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ChemicalBook CAS DataBase List Testosterone acetate
1045-69-8

Testosterone acetate synthesis

11synthesis methods
A solution of 4.23 g (14.7 mmol) of testosterone in 8 ml of pyridine dried over potassium hydroxide overnight (5 g of KOH to 250 ml of pyridine) is prepared in a 250-ml flask equipped with magnetic stirring. The solution is cooled to 0° C. with a water/ice mixture. 4 ml of acetic anhydride is added to it dropwise. The reaction mixture is left to return to room temperature, and the solution is stirred overnight at RT. After the starting product is no longer found in analytical TLC, 30 ml of distilled water and 30 ml of ethyl acetate are poured into the flask, and the mixture is stirred. The phases are separated with a separating funnel, and the aqueous phase is extracted with 3×20 ml of ethyl acetate. The organic phases are combined, and the solution obtained is washed with 20 nil of distilled water, dried over anhydrous magnesium sulfate, and evaporated in a rotary evaporator. The product thus obtained is dried under reduced pressure using a vacuum pump for 4 hours to remove all the solvents. 4.8 g (yield=99.0%) of testosterone acetate is obtained.
Testosterone acetate
-

Yield:1045-69-8 100%

Reaction Conditions:

with pyridine;dmap at 20; for 24 h;Inert atmosphere;

Steps:

4.1. Testosterone-17β-acetate (S1)

Testosterone 4 (500 mg, 1.73 mmol) was dissolved in 2.5 mLacetic anhydride. Then, 4 mg (0.035 mmol) of DMAP and 0.25 mLof dry pyridine were added. The mixture was stirred at room temperaturefor 24 h. The reaction was quenched with water and themixture was extracted with ethyl acetate (3 30 mL). The organiclayers were dried (Na2SO4) and concentrated under reduced pressure.The crude product was used to the next step without furtherpurification (567 mg, 100% yield). The NMR spectral data wereaccordance with those reported in the literature [33]. S1: 1HNMR (500 MHz, CDCl3) d 5.73 (s, 1H), 4.60 (dd, J = 9.0, 8.0 Hz,1H), 2.48-2.25 (m, 4H), 2.18 (m, 1H), 2.04 (s, 3H), 2.03-1.98 (m,1H), 1.77-1.87 (m, 2H), 1.75-1.62 (m, 2H), 1.61-1.47 (m, 3H),1.46-1.26 (m, 2H), 1.21-1.16 (m, 1H), 1.19 (s, 3H), 1.05-0.9 (m,3H), 0.84 (s, 3H).

References:

Trafalis, Dimitrios;Geromichalou, Elena;Dalezis, Panagiotis;Nikoleousakos, Nikolaos;Sarli, Vasiliki [Steroids,2016,vol. 115,p. 1 - 8]

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