Hydrochloric Acid → Estra-1,3,5(10),7-tetraen-3-ol

HRID 1107196Notes

Reaction equation

HRID 1107196 reaction equation
[CH3:1][C@@:2]12[C:18](=O)[CH2:17][CH2:16][C@H:15]1[C:14]1[C@@H:5]([C:6]3[CH:7]=[CH:8][C:9]([OH:20])=[CH:10][C:11]=3[CH2:12][CH:13]=1)[CH2:4][CH2:3]2.NN.[OH-].[K+].Cl>C(O)COCCO.O>[CH3:1][C@:2]12[CH2:3][CH2:4][C@H:5]3[C:14](=[CH:13][CH2:12][C:11]4[CH:10]=[C:9]([OH:20])[CH:8]=[CH:7][C:6]=43)[C@@H:15]1[CH2:16][CH2:17][CH2:18]2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 9321HydrazineHCID 14797Potassium HydroxideHCID 223368Equilin

Product 1

HCID 15870996Estra-1,3,5(10),7-tetraen-3-ol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8117Diethylene GlycolSolvent

Conditions

Temperature
207 °C

Procedure

To a suspension of equilin (100.2 mg, 0.3733 mmol) in 2 ml of diethylene glycol were added hydrazine (59 μL, 1.9 mmol) and potassium hydroxide (0.04 g, 0.7 mmol). The mixture was stirred in an oil bath at 200-214° C. for 2 h, after which the cooled reaction was diluted with 10 ml of water, neutralized with 1N HCl, and extracted three times with 25 ml of ether. The combined organic extracts were washed with 10 ml of brine, dried over magnesium sulfate, filtered, concentrated, and purified by preparative TLC (silica gel, 15% ethyl acetate/hexane eluent) to give a yellow resin.

Workup

  1. customafter which the cooled reaction
  2. extractionextracted three times with 25 ml of ether
  3. washThe combined organic extracts were washed with 10 ml of brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by preparative TLC (silica gel, 15% ethyl acetate/hexane eluent)
  8. customto give a yellow resin

Sources & evidence

ORD record
ord-895db49b32124a8aafe4b7ca25067471
Source dataset
uspto-grants-2000_05
Patent number
US06057439

Reaction notes

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