Dimethyl Sulfate → 1,3-Dimethoxyestra-1,3,5(10)-trien-17-one

HRID 839760Notes

Reaction equation

HRID 839760 reaction equation
[OH:1][C:2]1[C:19]2[C@@H:18]3[C@H:9]([C@H:10]4[C@@:14]([CH2:16][CH2:17]3)([CH3:15])[C:13](=[O:20])[CH2:12][CH2:11]4)[CH2:8][CH2:7][C:6]=2[CH:5]=[C:4]([O:21][CH3:22])[CH:3]=1.S(OC)(O[CH3:27])(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:27][O:1][C:2]1[C:19]2[C@@H:18]3[C@H:9]([C@H:10]4[C@@:14]([CH2:16][CH2:17]3)([CH3:15])[C:13](=[O:20])[CH2:12][CH2:11]4)[CH2:8][CH2:7][C:6]=2[CH:5]=[C:4]([O:21][CH3:22])[CH:3]=1

Participants

5

Reactant 3

HCID 6497Dimethyl Sulfate2×HCID 11430Potassium CarbonateHCID 545489061-Hydroxy-3-methoxyestra-1,3,5(10)-trien-17-one

Product 1

HCID 537114841,3-Dimethoxyestra-1,3,5(10)-trien-17-one

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A suspension of 1-hydroxy-3-methoxyestra-1,3,5(10)-trien-17-one (2.5 g, 8.3 mM), dimethyl sulfate (1.3 g, 10.3 mM) and potassium carbonate (1.2 g) in 250 ml of anhydrous acetone is refluxed with vigorous stirring for 6 hrs. An additional 0.5 g of dimethyl sulfate is added and the suspension refluxed for 14 hrs. The reaction mixture is filtered while warm and the solids washed well with acetone. The combined acetone filtrates are evaporated in vacuo and the residue is recrystallized from methanol-H2O. Two recrystallizations give 1,3-dimethoxyestra-1,3,5(10)-trien-17-one, yield 1.91 g (73%); m.p. 132°-133°.

Workup

  1. temperatureis refluxed
  2. temperaturethe suspension refluxed for 14 hrs
  3. filtrationThe reaction mixture is filtered
  4. temperaturewhile warm
  5. washthe solids washed well with acetone
  6. customThe combined acetone filtrates are evaporated in vacuo
  7. customthe residue is recrystallized from methanol-H2O
  8. customTwo recrystallizations

Sources & evidence

ORD record
ord-4424f8ccdde842ada0fad0c8f77c8924
Source dataset
uspto-grants-1978_06
Patent number
US04096253

Reaction notes

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