Реакция #81725

ord-e1717645044a464f8aa75e660cd0f8f3

Уравнение реакции

COC(=O)c1ccc2c(c1)CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](C(=O)c3ccccc3)CC[C@@H]12
methyl 17β-benzoyl-estra-1,3,5(10)-triene-3-carboxylate
O=C([O-])[O-].[K+].[K+]
K2CO3
O
water
→
C[C@]12CC[C@@H]3c4ccc(C(=O)O)cc4CC[C@H]3[C@@H]1CC[C@@H]2C(=O)c1ccccc1
title compound
C[C@]12CC[C@@H]3c4ccc(C(=O)O)cc4CC[C@H]3[C@@H]1CC[C@@H]2C(=O)c1ccccc1
17β-Benzoyl-estra-1,3,5(10)-triene-3-carboxylic Acid

Реактанты

COC(=O)c1ccc2c(c1)CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](C(=O)c3ccccc3)CC[C@@H]12
methyl 17β-benzoyl-estra-1,3,5(10)-triene-3-carboxylate
O=C([O-])[O-].[K+].[K+]
K2CO3
O
water

Реагенты

Нет

Растворители

CO
methanol

Условия реакции

Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    Температураis heated
  2. 2
    Температураat reflux for 5 h
  3. 3
    ДругоеThe volatiles are then removed at reduced pressure
  4. 4
    workup.ADDITIONthe residue is diluted with water
  5. 5
    Экстракцияextracted with EtOAc
  6. 6
    ЭкстракцияThe organic extract
  7. 7
    Промывкаis washed with water and brine
  8. 8
    Другоеdried
  9. 9
    Другоеevaporated

Методика

A mixture of methyl 17β-benzoyl-estra-1,3,5(10)-triene-3-carboxylate, K2CO3, water and methanol is heated at reflux for 5 h. The volatiles are then removed at reduced pressure and the residue is diluted with water, acidified with dilute aqueous HCl, and extracted with EtOAc. The organic extract is washed with water and brine, dried, and evaporated to yield the title compound.

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US05618806uspto-grants-1997_04