反应 #5434

ord-5496bc558f464336aaaccae32ef16785

反应方程式

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
收率 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
收率 69.6%

反应物

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

试剂

无

溶剂

C1CCOC1
tetrahydrofuran
C1CCOC1
tetrahydrofuran

反应条件

详细条件
See reaction.notes.procedure_details.

后处理

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

实验过程

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.

来源

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