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ChemicalBook CAS DataBase List Desogestrel
54024-22-5

Desogestrel synthesis

10synthesis methods
-

Yield:54024-22-5 89%

Reaction Conditions:

Stage #1:trimethylsilylacetylene with n-hexyllithium in tetrahydrofuran;hexane at -5; for 0.5 h;
Stage #2:11-methylene-18a-homo-estr-4-en-17-one in tetrahydrofuran;hexane at 0 - 5; for 1 h;

Steps:

17 Example 17. Synthesis of Desoqestrel (ethynylation reaction)
To a solution of hexillithium (3.0 g 2.3 M in hexane) in hexane (5 mL) cooled at - 5°C, a solution of trimethylsilyl acetylene (1 .32 g) in 6.8 mL of a mixture of THF/hexane1/7 was slowly added. The reaction mixture was stirred at -5°C for 30 mm, then asolution of compound 14 (1 .0 g) in 8 mL of hexane was added and the mixture stirred for 1 h at 0/5°C. Aqueous NaCI solution (8.5 mL) was added and the phases were separated. The organic phase was mixed with 5 mL of methanol, followed by addition of 1.5 mL of aqueous NaOH 30% and stirred for 4 h further. 10 mL of an aqueous solution of 3% Acetic acid was added. The phases were separated and the organicphase was washed with water (5.0 mL). The solvent was evaporated under reduced pressure and the residue dissolved in 1 mL of MeOH. The solvent was evaporated under reduced pressure and the residue dissolved in 2 mL of Hexane. The crude obtained was dissolved in 4 mL of hexane by heating at 60°C. The solution was cooled slowly in an ice bath and the resulting solid filtered, washed with 1 mL of cold hexaneand dried at 40°C under vacuum, to yield 0.89 g of Desogestrel (89%).

References:

BIONICE, S.L.U;SANDOVAL RODRíGUEZ, Celso Miguel;HERRáIZ SIERRA, Ignacio;MESSINA, Ivano;IGLESIAS RETUERTO, Jesús Miguel WO2017/149091, 2017, A1 Location in patent:Page/Page column 36; 37

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