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HRID1606487

反应详情

EQUATION

反应方程式

HRID 1606487 的结构方程式

REACTANTS

反应物

3
结构：CCN(CC)CC
HCID8471

Triethylamine

C6H15N

结构：COP(OC)OC
HCID8472

Trimethyl phosphite

C3H9O3P

结构：CC1([C@H]2CC[C@H]3[C@@H]4CC[C@H]5CC(=O)C(=CO)C[C@]5(C)[C@H]4C(=O)C[C@]23C)OCCO1
HCID86733331

未命名化合物

PRODUCTS

生成物

1
结构：C[C@@H]1C[C@@]2(C)[C@@H](CC[C@H]3[C@@H]4CC[C@H](C5(C)OCCO5)[C@@]4(C)CC(=O)[C@@H]32)CC1=O
HCID86733330

未命名化合物

收率 6.7%

AUXILIARIES

试剂、催化剂与溶剂

2
结构：Cl.Cl.O.[Cl][Ir]([Cl])([Cl])[Cl]
催化剂HCID16211483

Tetrachloroiridium--hydrogen chloride--water (1/2/1)

H4Cl6IrO

结构：CC(C)O
溶剂HCID3776

Isopropanol

C3H8O

PROCEDURE

实验过程

A solution of chloroiridic acid (30 mg.) and trimethyl phosphite (4.5 ml.) in aqueous 90% isopropanol (60 ml.) was heated under reflux for 17 hr. The solution was then neutralised with triethylamine and 20,20-ethylenedioxy 2-hydroxymethylene-5α-pregnane-3,11-dione (2 g.) was added. The mixture was heated under reflux for 40 hr. then cooled and partitioned between water and methylene chloride. The organic layer was dried (MgSO4) and evaporated in vacuo. The residue (1.94 g.) was subjected to preparative t.l.c. giving two fractions. The less polar fraction (0.18 g.) was crystallised from methanol to give 20,20-ethylenedioxy-2α-methyl-5α-pregnane-3,11-dione (0.13 g.), m.p. 179°-180°, [α]D + 77.5°.

WORKUP

后处理

  1. temperatureunder reflux for 17 hr
  2. additionwas added
  3. temperatureThe mixture was heated
  4. temperatureunder reflux for 40 hr
  5. temperaturethen cooled
  6. custompartitioned between water and methylene chloride
  7. dry with materialThe organic layer was dried (MgSO4)
  8. customevaporated in vacuo
  9. customgiving two fractions
  10. customThe less polar fraction (0.18 g.) was crystallised from methanol