تفاعل #7508

ord-faa2f348d6f5478eb5c5bd468fd5e72f

معادلة التفاعل

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
المردود 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
المردود 94.8%

المتفاعلات

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

الكواشف

لا شيء

المذيبات

CCOC(C)=O
EtOAc
c1ccccc1
benzene

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    درجة الحرارةrefluxed
  2. 2
    غسيلwashed twice with brine
  3. 3
    أخرىdried on Na2SO4
  4. 4
    أخرىthe solvents removed under reduced pressure

الإجراء التجريبي

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.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US07087590B2uspto-grants-2006_08