Hydrochloric Acid → Estra-1,3,5(10),6-tetraen-3-ol

HRID 1781931Notes

Reaction equation

HRID 1781931 reaction equation
[CH3:1][C@:2]12[CH2:18][CH2:17][C@H:16]3[C@@H:7]([CH:8]=[CH:9][C:10]4[CH:11]=[C:12]([OH:19])[CH:13]=[CH:14][C:15]=43)[C@@H:6]1[CH2:5][CH2:4][C:3]2=O.NN.[OH-].[K+].Cl>C(O)COCCO.O>[CH3:1][C@:2]12[CH2:18][CH2:17][C@H:16]3[C@@H:7]([CH:8]=[CH:9][C:10]4[CH:11]=[C:12]([OH:19])[CH:13]=[CH:14][C:15]=43)[C@@H:6]1[CH2:5][CH2:4][CH2:3]2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 9321HydrazineHCID 14797Potassium HydroxideHCID 1022253-Hydroxyestra-1,3,5(10),6-tetraen-17-one

Product 1

HCID 15480542Estra-1,3,5(10),6-tetraen-3-ol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8117Diethylene GlycolSolvent

Procedure

Estra-1,3,5(10),6-tetraen-3-ol-17-one (91.1 mg, 0.339 mmol), hydrazine (54 μL, 1.7 mmol), and potassium hydroxide (0.06 g) in 1.8 mL of diethylene glycol were heated in a 200° C. bath under argon for 2 h. After cooling to RT 10 mL of water were added and the solution was acidified to pH≈2 with 1N HCl. The resulting suspension was extracted three times with 10 mL of ether and the combined organic extracts were washed with 10 mL of brine, dried over magnesium sulfate, filtered through Celite, and concentrated under reduced pressure. The crude solid was purified by preparative TLC (25% ethyl acetate/hexane on silica gel) to give product homogeneous to TLC (5.9 mg, 23 μmol, 7%).

Workup

  1. additionwere added
  2. extractionThe resulting suspension was extracted three times with 10 mL of ether
  3. washthe combined organic extracts were washed with 10 mL of brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered through Celite
  6. concentrationconcentrated under reduced pressure
  7. customThe crude solid was purified by preparative TLC (25% ethyl acetate/hexane on silica gel)
  8. customto give product homogeneous to TLC (5.9 mg, 23 μmol, 7%)

Sources & evidence

ORD record
ord-13e55dc3a2d64554a99a1dd2a344d976
Source dataset
uspto-grants-1997_05
Patent number
US05633392

Reaction notes

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