Estrone → Estrone

HRID 1578755Notes

Reaction equation

HRID 1578755 reaction equation
S([O:6][CH3:7])(OC)(=O)=O.[CH3:8][C@@:9]12[C:25](=[O:26])[CH2:24][CH2:23][C@H:22]1[C@H:21]1[C@@H:12]([C:13]3[CH:14]=[CH:15][C:16]([OH:27])=[CH:17][C:18]=3[CH2:19][CH2:20]1)[CH2:11][CH2:10]2.[OH-].[K+]>O1CCCC1>[CH3:8][O:6][CH3:7].[CH3:8][C@@:9]12[C:25](=[O:26])[CH2:24][CH2:23][C@H:22]1[C@H:21]1[C@@H:12]([C:13]3[CH:14]=[CH:15][C:16]([OH:27])=[CH:17][C:18]=3[CH2:19][CH2:20]1)[CH2:11][CH2:10]2

Participants

6

Reactant 3

HCID 5870EstroneHCID 6497Dimethyl SulfateHCID 14797Potassium Hydroxide2×

Product 2

HCID 5870EstroneHCID 8254Dimethyl Ether

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Into a mixture of 0.39 ml of dimethyl sulfate and 5 ml of tetrahydrofuran, 1 g of estrone and 0.76 ml of 30% KOH aqueous solution dissolved in 5 ml of tetrahydrofuran were added over a period of one hour. The reaction temperature was maintained at 15° - 20°C. The resulting mixture was stirred for one hour. Then, after the addition of 10 ml of 1% KOH aqueous solution, Example 1 was repeated to obtain 1.049 g of the 100% purity methyl ether of estrone in a 99.8% yield.

Workup

  1. additionwere added over a period of one hour
  2. temperatureThe reaction temperature was maintained at 15° - 20°C

Sources & evidence

ORD record
ord-b2d882a54dfe4c5db615605d6a91ed06
Source dataset
uspto-grants-1976_02
Patent number
US03939186

Reaction notes

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