Estrone → Estrone

HRID 1578751Notes

Reaction equation

HRID 1578751 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.S(OC)(OC)(=O)=O.[O:28]1[CH2:32]CC[CH2:29]1.[OH-].[K+]>O>[CH3:29][O:28][CH3:32].[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

Participants

7

Reactant 4

HCID 5870EstroneHCID 6497Dimethyl SulfateHCID 8028TetrahydrofuranHCID 14797Potassium Hydroxide

Product 2

HCID 5870EstroneHCID 8254Dimethyl Ether

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a mixture of 1 g of estrone, 0.5 ml of dimethyl sulfate and 5 ml of tetrahydrofuran, 6 ml of 10% aqueous solution of potassium hydroxide was added over a period of one hour. The reaction temperature was maintained at 15° - 20°C during the addition. The resulting mixture was stirred for one hour to complete the etherification. Then, 6 ml of water was added, and tetrahydrofuran was distilled under atmospheric pressure. The crystals which formed during the distillation were filtered from the cooled reaction mixture, washed with water and dried to obtain 1.048 g of the 100% purity methyl ether of estrone in a 99.7% yield.

Workup

  1. additionwas added over a period of one hour
  2. temperatureThe reaction temperature was maintained at 15° - 20°C during the addition
  3. distillationtetrahydrofuran was distilled under atmospheric pressure
  4. customThe crystals which formed during the distillation
  5. filtrationwere filtered from the cooled reaction mixture
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-2e3bf2fe3de8472b8c76a021441cd175
Source dataset
uspto-grants-1976_02
Patent number
US03939186

Reaction notes

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