反応 #5434

ord-5496bc558f464336aaaccae32ef16785

反応方程式

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
CCCC[N+](CCCC)(CCCC)CCCC.[F-]
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
収率 69.6%
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
11beta-(4-Acetylphenyl)-17alpha-hydroxy-17-(2-propinyl)14beta-estra-4,9-dien-3-one
収率 69.6%

反応物

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
CCCC[N+](CCCC)(CCCC)CCCC.[F-]
tetrabutylammonium fluoride
—
solution

試薬

なし

溶媒

C1CCOC1
tetrahydrofuran
C1CCOC1
tetrahydrofuran

反応条件

詳細条件
See reaction.notes.procedure_details.

後処理

  1. 1
    workup.ADDITIONIt is poured on water
  2. 2
    抽出extracted with ethyl acetate
  3. 3
    洗浄The combined organic phases are washed with water
  4. 4
    その他dried on sodium sulfate
  5. 5
    濃縮concentrated by evaporation
  6. 6
    その他The residue is chromatographed with a mixture of hexane/ethyl acetate on silica gel

実験手順

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.

出典

DOI: 10.6084/m9.figshare.5104873.v1特許: US05244886uspto-grants-1993_09