ChemicalBook CAS DataBase List 13-ethyl-3-methoxygona-2,5(10)-dien-17beta-ol

13-ethyl-3-methoxygona-2,5(10)-dien-17beta-ol synthesis

5synthesis methods

Product Name:13-ethyl-3-methoxygona-2,5(10)-dien-17beta-ol
CAS Number:14507-49-4
Molecular formula:C20H30O2
Molecular Weight:302.45

13-Ethyl-3-methoxygona-1,3,5(10),8-tetraen-17beta-ol

7443-72-3
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13-ethyl-3-methoxygona-2,5(10)-dien-17beta-ol

14507-49-4
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Yield:14507-49-4 86%

Reaction Conditions:

Stage #1:18-methyl-3-methoxy-1,3,5(10),8-estratetraen-17β-ol with sodium;aniline in tetrahydrofuran at -10 - 0; for 2 h;
Stage #2: with acetic acid in tetrahydrofuran;methanol;water at 0 - 40; for 1.66667 h;Temperature;Reagent/catalyst;Solvent;

Steps:

1 Example 1
(1) Reducing reagent preparationTake 30ml of aniline in a 250ml four-necked flask and cool the aniline to -5°C.5g of sodium metal was added 5 times in 20 minutes, and the temperature of the reaction system was controlled at -10 to 0°C.The reaction solution was gradually warmed to 60 to 70° C. The reaction solution gradually turned blue and was stirred at a constant temperature for 1 hour. (2) Reduction reactionTake 5g of 18-methyl-3-methoxy-1,3,5(10),8-estratetraen-17β-ol (ethyl hydride),50 ml of tetrahydrofuran was placed in a single-necked flask and dissolved by stirring. Cool the solution to -100°C,An ethyl hydride/tetrahydrofuran solution was slowly added dropwise to the sodium anilino solution over 30 minutes.After 1.5 hours of the heat preservation reaction, the temperature of the reaction system was lowered to 0°C, and 25 ml of methanol was added dropwise in 30 minutes.The control material was incubated at 0 to 10°C for 30 minutes with stirring. Transfer the reaction solution to a 500 ml reaction flask, add 150 ml of water, and stir for 10 minutes.Add 30% acetic acid solution 200ml, control the temperature of the reaction system at 30 ~ 40 °C, hold for 30 minutes, filter, filter cake washed to neutral, dry, wet weight 5.1g.The above wet product and 10 ml of ethanol were added to a 100 ml single-mouth flask, heated to reflux, and stirred for 1 hour.After cooling to room temperature, the mixture was cooled at -5 to 0°C for 16 hours and suction filtered. Wash the filter cake with 2 ml of industrial ethanol and drain it.The filter cake was placed in a hot air circulation oven and dried at 40° C. to constant weight to obtain 4.3 g dry weight of ethyllithium ammonia, with a yield of 86%.HPLC purity is 97.8%.

References:

Jiangxi Yuneng Pharmaceutical Co., Ltd.;Deng Lianqiang;Zhu Feilun CN107955053, 2018, A Location in patent:Paragraph 0028-0057

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