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

HRID 1603345ノート

反応式

HRID 1603345 の反応式
[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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 24611Copper bromide (CuBr2)触媒HCID 6342Acetonitrile溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-88eb9028f67a4aaca4cca963d6fdf876
出典データセット
uspto-grants-1999_11
特許番号
US05986115

反応ノート

読み込み中…