Estrone → 1428-66-6

HRID 1767420Notes

Reaction equation

HRID 1767420 reaction equation
[CH3:1][C@@:2]12[C:18](=[O:19])[CH2:17][CH2:16][C@H:15]1[C@H:14]1[C@@H:5]([C:6]3[CH:7]=[CH:8][C:9]([OH:20])=[CH:10][C:11]=3[CH2:12][CH2:13]1)[CH2:4][CH2:3]2.C(=O)([O-])[O-].[K+].[K+].Br[CH2:28][C:29]([O:31]CC)=[O:30]>CC(C)=O>[CH3:1][C@:2]12[CH2:3][CH2:4][C@H:5]3[C@@H:14]([CH2:13][CH2:12][C:11]4[CH:10]=[C:9]([O:20][CH2:28][C:29]([OH:31])=[O:30])[CH:8]=[CH:7][C:6]=43)[C@@H:15]1[CH2:16][CH2:17][C:18]2=[O:19]

Participants

5

Reactant 3

HCID 5870EstroneHCID 7748Ethyl bromoacetateHCID 11430Potassium Carbonate

Product 1

HCID 2252891428-66-6Yield 37.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The mixture of estrone (540 mg, 2.0 mmol), potassium carbonate (910 mg, 6.6 mmol), ethyl bromoacetate (500 mg, 3.0 mmol), and acetone (25 ml) was refluxed for 6 h. After cooling, the mixture was filtered to remove potassium carbonate. The filtrate was concentrated under reduced pressure. To this residue, 10 ml dioxane and 14 ml 5% sodium hydroxide solution were added. After the mixture was stirred at room temperature overnight, it was acidified with concentrated hydrochloric acid to pH 2, and then extracted three times with ethyl acetate (15 ml each). The organic phases were combined, washed with water and brine, dried over magnesium sulfate, filtered, and then evaporated in vacuo. The residue was recrystallized from ethanol to give 246 mg estra-1,3,5(10)-trien-17-one-3-oxyacetic acid as white crystals, mp 205-208° C.

Workup

  1. temperaturewas refluxed for 6 h
  2. temperatureAfter cooling
  3. filtrationthe mixture was filtered
  4. customto remove potassium carbonate
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. additionTo this residue, 10 ml dioxane and 14 ml 5% sodium hydroxide solution were added
  7. extractionextracted three times with ethyl acetate (15 ml each)
  8. washwashed with water and brine
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered
  11. customevaporated in vacuo
  12. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-44ff0476a56d4c9e955a925478c8b819
Source dataset
uspto-grants-2007_06
Patent number
USRE039707E1

Reaction notes

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