反应 #7508

ord-faa2f348d6f5478eb5c5bd468fd5e72f

反应方程式

OCCO
ethylene glycol
Cc1ccc(S(=O)(=O)[O-])cc1.c1cc[nH+]cc1
pyridinium p-toluenesulfonate
CCCCCC.CCOC(C)=O
EtOAc Hexane
C[C@]12CC[C@H]3[C@@H](CC[C@@H]4CC(O)CC[C@@H]43)[C@@H]1CCC2=O
Compound 4
C[C@]12CC[C@H]3[C@@H](CC[C@@H]4CC(O)CC[C@@H]43)[C@@H]1CCC2=O
3-hydroxy-5βestran-17-one
→
C[C@]12CC[C@H]3[C@@H](CC[C@@H]4CC(O)CC[C@@H]43)[C@@H]1CCC21OCCO1
title compound
收率 94.8%
C[C@]12CC[C@H]3[C@@H](CC[C@@H]4CC(O)CC[C@@H]43)[C@@H]1CCC21OCCO1
3-hydroxy-5β-estran-17-one ethylene ketal
收率 94.8%

反应物

OCCO
ethylene glycol
Cc1ccc(S(=O)(=O)[O-])cc1.c1cc[nH+]cc1
pyridinium p-toluenesulfonate
CCCCCC.CCOC(C)=O
EtOAc Hexane
C[C@]12CC[C@H]3[C@@H](CC[C@@H]4CC(O)CC[C@@H]43)[C@@H]1CCC2=O
Compound 4
C[C@]12CC[C@H]3[C@@H](CC[C@@H]4CC(O)CC[C@@H]43)[C@@H]1CCC2=O
3-hydroxy-5βestran-17-one

试剂

无

溶剂

CCOC(C)=O
EtOAc
c1ccccc1
benzene

反应条件

详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    温度refluxed
  2. 2
    洗涤washed twice with brine
  3. 3
    其他dried on Na2SO4
  4. 4
    其他the solvents removed under reduced pressure

实验过程

Compound 4(10 g, 36.2 mmol) was dissolved in dry benzene (150 ml) mixed with ethylene glycol (25 ml, 280 mmol) and pyridinium p-toluenesulfonate (1 g, 3.9 mmol) and refluxed using a Dean-stark separator overnight till no starting material was detected by TLC. The cold solution was diluted with EtOAc (100 ml), washed twice with brine, dried on Na2SO4 and the solvents removed under reduced pressure. Flash-chromatography on silica gel with EtOAc: Hexane 4:6 as eluant to give 11.0 g (94.5% yield) the title compound as a white solid.

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: US07087590B2uspto-grants-2006_08