Реакция #5434

Уравнение реакции

11beta-(4-Acetylphenyl)-17alpha-hydroxy-17-(3-trimethysilyl-2-propinyl)-14beta-estra-4,9-dien-3-one

tetrabutylammonium fluoride

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title compound

Выход 69.6%

11beta-(4-Acetylphenyl)-17alpha-hydroxy-17-(2-propinyl)14beta-estra-4,9-dien-3-one

Выход 69.6%

Растворители

tetrahydrofuran

tetrahydrofuran

Условия реакции

Обработка

1. 1
   workup.ADDITIONIt is poured on water
2. 2
   Экстракцияextracted with ethyl acetate
3. 3
   ПромывкаThe combined organic phases are washed with water
4. 4
   Другоеdried on sodium sulfate
5. 5
   Концентрированиеconcentrated by evaporation
6. 6
   ДругоеThe residue is chromatographed with a mixture of hexane/ethyl acetate on silica gel

Методика

470 mg of 11beta-(4-Acetylphenyl)-17alpha-hydroxy-17-(3-trimethysilyl-2-propinyl)-14beta-estra-4,9-dien-3-one in 24 ml of tetrahydrofuran is mixed with 2.35 ml of a 1M solution of tetrabutylammonium fluoride in tetrahydrofuran and stirred for 5 minutes at room temperature. It is poured on water and extracted with ethyl acetate. The combined organic phases are washed with water, dried on sodium sulfate and concentrated by evaporation. The residue is chromatographed with a mixture of hexane/ethyl acetate on silica gel. 280 mg of the title compound is isolated as foam.

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