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Water → 7alpha-(5-Acetoxypentyl)-3-hydroxy-estra-1,3,5(10)-trien-17-one

HRID 1595967
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인쇄 미리보기

반응식

HRID 1595967 반응식
[Br-].[Li+].[C:3]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C@@H:12]1[CH2:29][C:28]2[C@H:23]([CH2:24][CH2:25][C:26](=[O:30])[CH:27]=2)[C@@H:22]2[C@@H:13]1[C@H:14]1[C@@:18]([CH2:20][CH2:21]2)([CH3:19])[C:17](=[O:31])[CH2:16][CH2:15]1)(=[O:5])[CH3:4].O>C(#N)C.[Cu](Br)Br>[C:3]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C@@H:12]1[CH2:29][C:28]2[CH:27]=[C:26]([OH:30])[CH:25]=[CH:24][C:23]=2[C@@H:22]2[C@@H:13]1[C@H:14]1[C@@:18]([CH2:20][CH2:21]2)([CH3:19])[C:17](=[O:31])[CH2:16][CH2:15]1)(=[O:5])[CH3:4]
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참가 물질

6

반응물 3

HCID 962WaterHCID 82050Lithium BromideHCID 15838157HCID 15838157, 화합물

생성물 1

HCID 158381587alpha-(5-Acetoxypentyl)-3-hydroxy-estra-1,3,5(10)-trien-17-one수율 73.8%

시약·촉매·용매 2

HCID 24611Copper bromide (CuBr2)촉매HCID 6342
Acetonitrile
용매

실험 절차

17.8 g of lithium bromide and 92.83 g of copper(II) bromide are added to a solution of 82.3 g of 7α-(5-acetoxypentyl)-estr-4-ene-3,17-dione in 936 ml of acetonitrile at a bath temperature of 80° C. After 10 minutes at a bath temperature of 80° C., the reaction solution is cooled, mixed with water, extracted three times with ethyl acetate, the organic phase is washed with water and sodium bicarbonate solution and dried. The residue that is obtained after the concentration by evaporation is chromatographed on silica gel, and 60.4 g of 7α-(5-acetoxypentyl)-3-hydroxy-estra-1,3,5(10)-trien-17-one is obtained as an oil.

후처리

  1. temperaturethe reaction solution is cooled
  2. extractionextracted three times with ethyl acetate
  3. washthe organic phase is washed with water and sodium bicarbonate solution
  4. customdried
  5. customThe residue that is obtained
  6. concentrationafter the concentration
  7. customby evaporation
  8. customis chromatographed on silica gel

출처 및 근거

ORD 기록
ord-f78c164df42b4672803353e2077ea925
출처 데이터셋
uspto-grants-2001_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06288051B1

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