反応 #7508

ord-faa2f348d6f5478eb5c5bd468fd5e72f

反応方程式

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
収率 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
収率 94.8%

反応物

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

試薬

なし

溶媒

CCOC(C)=O
EtOAc
c1ccccc1
benzene

反応条件

詳細条件
See reaction.notes.procedure_details.

後処理

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

実験手順

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.

出典

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