Réaction #5434

ord-5496bc558f464336aaaccae32ef16785

Équation de réaction

CC(=O)c1ccc([C@H]2C[C@@]3(C)[C@H](CC[C@]3(O)CC#C[Si](C)(C)C)[C@@H]3CCC4=CC(=O)CCC4=C32)cc1

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

tetrabutylammonium fluoride

→

C#CC[C@@]1(O)CC[C@@H]2[C@@H]3CCC4=CC(=O)CCC4=C3[C@@H](c3ccc(C(C)=O)cc3)C[C@@]21C

title compound

Rendement 69.6%

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

Rendement 69.6%

Réactifs

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

tetrabutylammonium fluoride

—

solution

Réactifs

Aucun

Solvants

tetrahydrofuran

Conditions de réaction

Conditions détaillées

See reaction.notes.procedure_details.

Traitement

1
workup.ADDITIONIt is poured on water
2
Extractionextracted with ethyl acetate
3
LavageThe combined organic phases are washed with water
4
Autredried on sodium sulfate
5
Concentrationconcentrated by evaporation
6
AutreThe residue is chromatographed with a mixture of hexane/ethyl acetate on silica gel

Mode opératoire

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.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US05244886uspto-grants-1993_09