تفاعل #81725

ord-e1717645044a464f8aa75e660cd0f8f3

معادلة التفاعل

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

المتفاعلات

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

الكواشف

لا شيء

المذيبات

CO
methanol

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    درجة الحرارةis heated
  2. 2
    درجة الحرارةat reflux for 5 h
  3. 3
    أخرىThe volatiles are then removed at reduced pressure
  4. 4
    workup.ADDITIONthe residue is diluted with water
  5. 5
    استخلاصextracted with EtOAc
  6. 6
    استخلاصThe organic extract
  7. 7
    غسيلis washed with water and brine
  8. 8
    أخرىdried
  9. 9
    أخرىevaporated

الإجراء التجريبي

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.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US05618806uspto-grants-1997_04