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HRID746157

反应详情

EQUATION

反应方程式

HRID 746157 的结构方程式

REACTANTS

反应物

2
结构：C[C@]12CCC3=C4CCC(=O)C=C4CC[C@H]3[C@@H]1C=CC2=O
HCID13423612

未命名化合物

结构：[Li]C
HCID178418348

未命名化合物

PRODUCTS

生成物

1
结构：C[C@@H]1CC(=O)[C@@]2(C)CCC3=C4CCC(=O)C=C4CC[C@H]3[C@H]12
HCID13423614

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

5
结构：[Cu][I]
催化剂HCID24350

Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)

CuI

结构：[I][Cu][I]
催化剂HCID83717

Copper iodide (CuI2)

CuI2

结构：N
溶剂HCID222

Ammonia gas

H3N

结构：CCOCC
溶剂HCID3283

Diethyl Ether

C4H10O

结构：C1CCOC1
溶剂HCID8028

Tetrahydrofuran

C4H8O

CONDITIONS

反应条件

温度
-20 °C

PROCEDURE

实验过程

5.2 ml of a 5% solution of methyllithium in diethyl ether are mixed with 570 mg of copper(I) iodide by portions at -5° C. Stirring is performed at a temperature between -5° and 0° C. until the copper iodide is fully dissolved. Then it is cooled to -20° C. and a solution of 1.1 g of 4,9,15-estratriene-3,17-dione in 15 ml of absolute tetrahydrofuran is slowly added drop by drop. It is stirred for 20 minutes at -20° C., then poured in concentrated aqueous ammonia solution and extracted with ethyl acetate. After chromatography with silica gel with hexane/ethyl acetate and crystallization of the main fraction from ethyl acetate/diisopropyl ether, 720 mg of 15β-methyl-4,9-estradiene-3,17-dione with a melting point of 125° to 126° C. are obtained.

WORKUP

后处理

  1. dissolutionis fully dissolved
  2. stirringIt is stirred for 20 minutes at -20° C.
  3. extractionextracted with ethyl acetate
  4. customAfter chromatography with silica gel with hexane/ethyl acetate and crystallization of the main fraction from ethyl acetate/diisopropyl ether, 720 mg of 15β-methyl-4,9-estradiene-3,17-dione with a melting point of 125° to 126° C.
  5. customare obtained