反应 #1162945

ord-5bb261c2b6a5418fb6020369d9a31e4d

反应方程式

[H][H]
hydrogen
C[C@]12CC[C@H](O)C[C@H]1CC[C@@H]1[C@@H]2C[C@@H](O)[C@]2(C)[C@@H](C3=CC(=O)OC3)CC[C@]12O
digoxigenin
O=O
oxygen
[H][H]
hydrogen
→
C[C@]12[C@H](O)CC3C(CC[C@@H]4CC(=O)CC[C@]34C)[C@@]1(O)CC[C@@H]2C1=CC(=O)OC1
3 - Dehydrodigoxigenin

反应物

[H][H]
hydrogen
C[C@]12CC[C@H](O)C[C@H]1CC[C@@H]1[C@@H]2C[C@@H](O)[C@]2(C)[C@@H](C3=CC(=O)OC3)CC[C@]12O
digoxigenin
O=O
oxygen
[H][H]
hydrogen

试剂

[O]=[Pt]
Platinum oxide

溶剂

O
water
CC(C)=O
acetone
O
water

反应条件

详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    其他The catalyst was removed by filtration
  2. 2
    洗涤washed with acetone
  3. 3
    workup.ADDITIONthe washings added to the filtrate
  4. 4
    浓缩the filtrate concentrated in vacuo
  5. 5
    workup.DISSOLUTIONThe residue was dissolved in chloroform
  6. 6
    洗涤washed with water
  7. 7
    干燥the solution dried (magnesium sulphate)
  8. 8
    其他Evaporation of the solvent in vacuo
  9. 9
    其他gave a gum which
  10. 10
    其他crystallised from acetone/ether
  11. 11
    其他[α] D25 + 39.1° (c = 0.48 in methanol)

实验过程

Platinum oxide (Adams' catalyst) (500 mg.) was suspended in water (50 ml.) and a continuous stream of hydrogen passed for 1 hour. The hydrogen was displaced by nitrogen and digoxigenin (2.0 g.), in acetone (200 ml.) and water (50 ml.), added. A continuous stream of oxygen was passed through the mixture for 18 hours. The catalyst was removed by filtration, washed with acetone, the washings added to the filtrate and the filtrate concentrated in vacuo. The residue was dissolved in chloroform, washed with water and the solution dried (magnesium sulphate). Evaporation of the solvent in vacuo gave a gum which crystallised from acetone/ether. The 3-dehydrodigoxigenin melted at 251.2°C. and had [α] D25 + 39.1° (c = 0.48 in methanol).

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: US03954739uspto-grants-1976_05