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

HRID 1603345노트

반응식

HRID 1603345 반응식
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C@@H:7]1[CH2:24][C:23]2[C@H:18]([CH2:19][CH2:20][C:21](=[O:25])[CH:22]=2)[C@@H:17]2[C@@H:8]1[C@H:9]1[C@@:13]([CH2:15][CH2:16]2)([CH3:14])[C:12](=[O:26])[CH2:11][CH2:10]1.[Br-].[Li+].O.C(=O)(O)[O-].[Na+]>C(#N)C.[Cu](Br)Br.C(OCC)(=O)C>[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C@@H:7]1[CH2:24][C:23]2[CH:22]=[C:21]([OH:25])[CH:20]=[CH:19][C:18]=2[C@@H:17]2[C@@H:8]1[C@H:9]1[C@@:13]([CH2:15][CH2:16]2)([CH3:14])[C:12](=[O:26])[CH2:11][CH2:10]1

참가 물질

8

반응물 4

HCID 962WaterHCID 82050Lithium BromideHCID 516892Sodium BicarbonateHCID 571565697alpha-(5-Chloropentyl)-estr-4-ene-3,17-dione

생성물 1

HCID 229418087alpha-(5-Chloropentyl)-3-hydroxy-estra-1,3,5(10)-trien-17-one수율 53%

시약·촉매·용매 3

HCID 24611Copper bromide (CuBr2)촉매HCID 6342Acetonitrile용매2회HCID 8857Ethyl Acetate용매

실험 절차

18.96 g of 7α-(5-chloropentyl)-estr-4-ene-3,17-dione is dissolved in 350 ml of anhydrous acetonitrile and mixed under inert gas at 80° C. with a solution of 4.36 g of lithium bromide and 22.5 g of copper(II) bromide in 390 ml of anhydrous acetonitrile. It is stirred for 5 more minutes, the mixture is cooled in an ice bath and mixed with water and ethyl acetate. The organic phase is shaken out with saturated sodium bicarbonate solution, the aqueous phase with ethyl acetate, the combined organic phases with saturated common salt solution, dried with sodium sulfate and concentrated by evaporation in a vacuum. The raw yield of 19.1 g is chromatographed on silica gel in hexane and ethyl acetate, whereby 10.0 g of oily 7α-(5-chloropentyl)-3-hydroxy-estra-1,3,5(10)-trien-17-one is obtained, which can be crystallized from hexane/dichloromethane.

후처리

  1. temperaturethe mixture is cooled in an ice bath
  2. dry with materialthe aqueous phase with ethyl acetate, the combined organic phases with saturated common salt solution, dried with sodium sulfate
  3. concentrationconcentrated by evaporation in a vacuum
  4. customThe raw yield of 19.1 g is chromatographed on silica gel in hexane and ethyl acetate

출처 및 근거

ORD 기록
ord-88eb9028f67a4aaca4cca963d6fdf876
출처 데이터셋
uspto-grants-1999_11
특허 번호
US05986115

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