반응 #7508

ord-faa2f348d6f5478eb5c5bd468fd5e72f

반응 방정식

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
수율 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
수율 94.8%

반응물

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

시약

없음

용매

CCOC(C)=O
EtOAc
c1ccccc1
benzene

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    온도refluxed
  2. 2
    세척washed twice with brine
  3. 3
    기타dried on Na2SO4
  4. 4
    기타the solvents removed under reduced pressure

실험 절차

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.

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US07087590B2uspto-grants-2006_08