Hydrochloric Acid → 2-Hydroxy-estradiol

HRID 1598939Notes

Reaction equation

HRID 1598939 reaction equation
CC([O:4][C@@H:5]1[C@@:9]2([CH3:24])[CH2:10][CH2:11][C@@H:12]3[C:21]4[C:16](=[CH:17][C:18]([OH:23])=[C:19]([OH:22])[CH:20]=4)[CH2:15][CH2:14][C@H:13]3[C@@H:8]2[CH2:7][CH2:6]1)=O.CO.Cl.C([O-])(O)=O.[Na+]>CCOC(C)=O.O>[CH3:24][C@@:9]12[C@@H:5]([OH:4])[CH2:6][CH2:7][C@H:8]1[C@H:13]1[C@@H:12]([C:21]3[CH:20]=[C:19]([OH:22])[C:18]([OH:23])=[CH:17][C:16]=3[CH2:15][CH2:14]1)[CH2:11][CH2:10]2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 1855442-Hydroxyestradiol 17-acetateHCID 516892Sodium Bicarbonate

Product 1

HCID 2473042-Hydroxy-estradiol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To the crude product (100 g) of 2-hydroxyestradiol 17-acetate obtained by the process described in Example 3-a, MeOH (3600 ml) and concentrated HCl (400 ml) were added, and the solution was refluxed for 1 hour. After the reaction mixture was cooled, water and AcOEt were added to it and the solution was neutralized by addition of NaHCO3, and extracted with AcOEt. The organic layer was washed with brine, and dried over anhydrous Na2SO4, and then evaporated in vacuo to obtain a crude product (68.7 g), which was, in turn, subjected to silica gel chromatography (elution solvent, hexane:AcOEt=1:1) to afford 59 g (91% from 2-acetylestradiol 17-acetate) of the titled compound.

Workup

  1. additionwere added
  2. temperaturethe solution was refluxed for 1 hour
  3. temperatureAfter the reaction mixture was cooled
  4. extractionextracted with AcOEt
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous Na2SO4
  7. customevaporated in vacuo
  8. customto obtain a crude product (68.7 g), which
  9. washsubjected to silica gel chromatography (elution solvent, hexane:AcOEt=1:1)

Sources & evidence

ORD record
ord-bdba5c2202194bbb80b8cf99024fcd3c
Source dataset
uspto-grants-1998_04
Patent number
US05739302

Reaction notes

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