Water → HCID 86734261, compound

HRID 1973497Notes

Reaction equation

HRID 1973497 reaction equation
[CH2:1]1[CH2:10][O:9][CH:8]2[CH:3]([C@:4]3([CH2:22][C:21](=[O:23])[C@H:20]4[C@@H:11]([CH2:12][CH2:13][C:14]5[CH:15]=[C:16]([O:24][CH3:25])[CH:17]=[CH:18][C:19]=54)[C@@H:6]3[CH2:7]2)[CH3:5])[O:2]1.[CH3:26]C(C)([O-])C.[K+].O>CI.C(O)(C)(C)C>[CH2:1]1[CH2:10][O:9][CH:8]2[CH:3]([C@:4]3([CH2:22][C:21](=[O:23])[C@@:20]4([CH3:26])[C@@H:11]([CH2:12][CH2:13][C:14]5[CH:15]=[C:16]([O:24][CH3:25])[CH:17]=[CH:18][C:19]=54)[C@@H:6]3[CH2:7]2)[CH3:5])[O:2]1

Participants

6

Reactant 3

HCID 962WaterHCID 23665647Potassium tert-butoxideHCID 68132042HCID 68132042, compound

Product 1

HCID 86734261HCID 86734261, compound

Reagents, catalysts & solvents 2

HCID 6328Methyl iodideSolventHCID 6386tert-ButanolSolvent

Procedure

To a stirred, ice cooled solution of 10.5 g of 17-ethylenedioxy-3-methoxyestra-1,3,5(10)-trien-11-one in 300 ml of methyl iodide under an atmosphere of nitrogen is added, over 10 minutes, 120 ml of a 1.1 molar solution of potassium tert.-butoxide in t-butyl alcohol. The temperature is allowed to rise to room temperature and the mixture is then stirred for 18 hours. It is next poured onto 500 ml of water and extracted with methylene chloride, twice. The combined organic extracts are washed with water and dried over sodium sulfate. Removal of the solvent gives an oil which is crystallized from ether to yield 17-ethylenedioxy-3-methoxy-9α-methylestra-1,3,5(10)-trien-11-one, m.p. 142° - 145° C.

Workup

  1. customto rise to room temperature
  2. extractionextracted with methylene chloride
  3. washThe combined organic extracts are washed with water
  4. dry with materialdried over sodium sulfate
  5. customRemoval of the solvent
  6. customgives an oil which
  7. customis crystallized from ether

Sources & evidence

ORD record
ord-b9f007cd42e34267860b6b01c66de2f6
Source dataset
uspto-grants-1976_12
Patent number
US03997574

Reaction notes

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