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HRID652217

反应详情

EQUATION

反应方程式

HRID 652217 的结构方程式

REACTANTS

反应物

2
结构：CC(=O)OC(C)=O
HCID7918

Acetic anhydride

C4H6O3

结构：C[C@]12CC[C@H](O)CC1=CC[C@@H]1[C@@H]2[C@@H](O)C[C@]2(C)C(=O)[C@H]3C[C@H]3[C@@H]12
HCID70445995

未命名化合物

PRODUCTS

生成物

1
结构：CC(=O)O[C@H]1CC[C@@]2(C)C(=CC[C@@H]3[C@@H]2[C@@H](O)C[C@]2(C)C(=O)[C@H]4C[C@H]4[C@@H]32)C1
HCID70046766

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

1
结构：c1ccncc1
溶剂HCID1049

Pyridine

C5H5N

PROCEDURE

实验过程

A solution of 7.9 g of 3β,11β-dihydroxy-15β,16β-methyleneandrost-5-en-17-one in 39.5 ml of pyridine and 39.5 ml of acetic anhydride is left to stand at room temperature for 5 hours, diluted with 800 ml of ice-water and, after standing for 1 hour, extracted with ethyl acetate. The organic phase is washed in succession with saturated sodium chloride solution, ice-cold dilute hydrochloric acid, ice-cold dilute sodium hydroxide solution and again with saturated sodium chloride solution, dried, and concentrated under a water-jet vacuum. Chromatography of the crude product over 30 times the amount by weight of silica gel and elution with a mixture of methylene chloride/acetone (98:2) yield 3β-acetoxy-11β-hydroxy-15β,16β-methyleneandrost-5-en-17-one which, after being dissolved and recrystallised once from methylene chloride/ether/petroleum ether, melts at 209°-211°.

WORKUP

后处理

  1. waitafter standing for 1 hour
  2. extractionextracted with ethyl acetate
  3. washThe organic phase is washed in succession with saturated sodium chloride solution, ice-cold dilute hydrochloric acid, ice-cold dilute sodium hydroxide solution and again with saturated sodium chloride solution
  4. customdried
  5. concentrationconcentrated under a water-jet vacuum
  6. washChromatography of the crude product over 30 times the amount by weight of silica gel and elution
  7. additionwith a mixture of methylene chloride/acetone (98:2)