Reaktion #5434

ord-5496bc558f464336aaaccae32ef16785

Reaktionsgleichung

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

Ausbeute 69.6%

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

Ausbeute 69.6%

Edukte

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

tetrabutylammonium fluoride

—

solution

Reagenzien

Keine

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Detaillierte Bedingungen

See reaction.notes.procedure_details.

Aufarbeitung

1
workup.ADDITIONIt is poured on water
2
Extraktionextracted with ethyl acetate
3
WaschenThe combined organic phases are washed with water
4
Sonstigedried on sodium sulfate
5
Einengenconcentrated by evaporation
6
SonstigeThe residue is chromatographed with a mixture of hexane/ethyl acetate on silica gel

Vorschrift

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.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05244886uspto-grants-1993_09