Hydrochloric Acid → HCID 68949346、化合物

HRID 650375ノート

反応式

HRID 650375 の反応式
[Br-].[Li+].[Cl:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C@@H:9]1[CH2:26][C:25]2[C@H:20]([CH2:21][CH2:22][C:23](=[O:27])[CH:24]=2)[C@@H:19]2[C@@H:10]1[C@H:11]1[C@@:15]([CH2:17][C@@H:18]2[F:28])([CH3:16])[C:14](=[O:29])[CH2:13][CH2:12]1.C(=O)(O)[O-].[Na+].Cl>C(#N)C.[Cu](Br)Br.O>[Cl:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C@@H:9]1[CH2:26][C:25]2[CH:24]=[C:23]([OH:27])[CH:22]=[CH:21][C:20]=2[C@@H:19]2[C@@H:10]1[C@H:11]1[C@@:15]([CH2:17][C@@H:18]2[F:28])([CH3:16])[C:14](=[O:29])[CH2:13][CH2:12]1

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 82050Lithium BromideHCID 516892Sodium BicarbonateHCID 688713657alpha-(5-Chloropentyl)-11beta-fluor-estr-4-ene-3,17-dione

生成物 1

HCID 68949346HCID 68949346、化合物収率 66.9%

試薬・触媒・溶媒 3

HCID 24611Copper bromide (CuBr2)触媒HCID 962Water溶媒HCID 6342Acetonitrile溶媒2 回

反応条件

温度
0 °C

実験手順

25.4 g of copper(II) bromide and 4.9 g of lithium bromide in 95 ml of anhydrous acetonitrile are added to 22.1 g of 7α-(5-chloropentyl)-11β-fluoro-estr-4-ene-3,17-dione in 160 ml of anhydrous acetonitrile at 80° C. After 20 minutes, the reaction mixture is cooled to 0° C., and 200 ml of saturated sodium bicarbonate solution is added in drops. Then, the solution is stirred into 750 ml of water, brought to pH=6 with 2N hydrochloric acid, extracted 3 times with ethyl acetate, washed with common salt solution, dried on magnesium sulfate and concentrated by evaporation in a vacuum. Chromatography of the crude product on silica gel with a hexane-ethyl acetate gradient yields 14.7 g of 7α-(5-chloropentyl)-11β-fluoro-3-hydroxy-estra-1,3,5(10)-trien-17-one.

後処理

  1. extractionextracted 3 times with ethyl acetate
  2. washwashed with common salt solution
  3. customdried on magnesium sulfate
  4. concentrationconcentrated by evaporation in a vacuum

出典と根拠

ORDレコード
ord-89b78e3294b347b7af40b48651e5f37a
出典データセット
uspto-grants-2001_08
特許番号
US06271403B1

反応ノート

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