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

HRID 5338
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HRID 5338 반응식
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C@H:10]2[CH2:27][C@@:25]3([CH3:26])[C@H:21]([CH2:22][CH2:23][C@:24]3([OH:35])[CH2:28][C:29]#[C:30][Si](C)(C)C)[C@H:20]3[C:11]2=[C:12]2[C:17]([CH2:18][CH2:19]3)=[CH:16][C:15](=[O:36])[CH2:14][CH2:13]2)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C@H:10]2[CH2:27][C@@:25]3([CH3:26])[C@H:21]([CH2:22][CH2:23][C@:24]3([OH:35])[CH2:28][C:29]#[CH:30])[C@H:20]3[C:11]2=[C:12]2[C:17]([CH2:18][CH2:19]3)=[CH:16][C:15](=[O:36])[CH2:14][CH2:13]2)=[CH:6][CH:5]=1)(=[O:3])[CH3:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 2724141Tetrabutylammonium FluorideHCID 1462340011beta-(4-Acetylphenyl)-17alpha-hydroxy-17-(3-trimethysilyl-2-propinyl)-14beta-estra-4,9-dien-3-one

생성물 1

HCID 1462340211beta-(4-Acetylphenyl)-17alpha-hydroxy-17-(2-propinyl)14beta-estra-4,9-dien-3-one수율 69.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  1. additionIt is poured on water
  2. extractionextracted with ethyl acetate
  3. washThe combined organic phases are washed with water
  4. customdried on sodium sulfate
  5. concentrationconcentrated by evaporation
  6. customThe residue is chromatographed with a mixture of hexane/ethyl acetate on silica gel

출처 및 근거

ORD 기록
ord-5496bc558f464336aaaccae32ef16785
출처 데이터셋
uspto-grants-1993_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05244886

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