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HRID1577859

反应详情

EQUATION

反应方程式

HRID 1577859 的结构方程式

REACTANTS

反应物

2
反应SMILES：N#CC1=C(C#N)C(=O)C(Cl)=C(Cl)C1=O
HCID6775

2,3-Dichloro-5,6-dicyano-p-benzoquinone

C8Cl2N2O2

反应SMILES：CC(=O)OCC(=O)[C@H]1[C@H](C)C[C@H]2[C@@H]3C[C@H](Cl)C4=CC(=O)CC[C@]4(C)[C@H]3[C@@H](O)C[C@@]21C
HCID70520093

未命名化合物

PRODUCTS

产物

1
反应SMILES：CC(=O)OCC(=O)[C@H]1[C@H](C)C[C@H]2[C@@H]3C[C@H](Cl)C4=CC(=O)C=C[C@]4(C)[C@H]3[C@@H](O)C[C@@]21C
HCID70518265

未命名化合物

收率 54.3%

AUXILIARIES

试剂、催化剂与溶剂

1
反应SMILES：C1COCCO1
溶剂HCID31275

1,4-Dioxane

C4H8O2

PROCEDURE

实验过程

2.0 g of 21-acetoxy-6α-chloro-11β-hydroxy-16α-methyl-4-pregnene-3,20-dione is dissolved in 100 ml of dioxane; 3 g of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone is added thereto and the mixture heated for 24 hours to boiling. After cooling, the mixture is vacuum-filtered from the undissolved matter, washed with dichloromethane, and concentrated under vacuum. The crude product is chromatographed on silica gel. With 37-46% acetone-hexane, after recrystallization from acetone-diisopropyl ether, 1.08 g of 21-acetoxy-6α-chloro-11βhydroxy-16α-methyl-1,4-pregnadiene-3,20-dione is obtained, m.p. 208.5° C. [α]D25 =+90° (chloroform). UV: ε243 =15,700 (methanol).

WORKUP

后处理

  1. temperaturethe mixture heated for 24 hours
  2. temperatureAfter cooling
  3. filtrationthe mixture is vacuum-filtered from the undissolved matter
  4. washwashed with dichloromethane
  5. concentrationconcentrated under vacuum
  6. customThe crude product is chromatographed on silica gel
  7. customWith 37-46% acetone-hexane, after recrystallization from acetone-diisopropyl ether