Реакция #81724

ord-310ecfb86a4b40d589cf751e84ec977e

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
    Температураwas heated
  2. 2
    Температураat reflux for 5 h
  3. 3
    ДругоеThe volatiles were then removed at reduced pressure
  4. 4
    workup.ADDITIONthe residue was diluted with water
  5. 5
    Экстракцияextracted with EtOAc
  6. 6
    ЭкстракцияThe organic extract
  7. 7
    Промывкаwas washed with water and brine
  8. 8
    Другоеdried
  9. 9
    Другоеevaporated to dryness

Методика

A mixture of methyl 17β-benzoyl-estra-1,3,5(10)-triene-3-carboxylate (60 mg, 0.15 mmol), K2CO3 (60 mg, 0.44 mmol), water (1 mL), and methanol (9 mL) was heated at reflux for 5 h. The volatiles were then removed at reduced pressure and the residue was diluted with water, acidified with dilute aqueous HCl, and extracted with EtOAc. The organic extract was washed with water and brine, dried, and evaporated to dryness. Trituration of the residue with acetone and methanol provided the title compound as a white solid, mp 240°-243° C.

Источник

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