Ammonia → HCID 86748619, compound

HRID 1654415Notes

Reaction equation

HRID 1654415 reaction equation
N.[Li].[CH2:3]1[CH2:16][O:15][C:10]23[O:11][CH2:12][CH2:13][O:14][C:5]2([C@:6]2([CH2:28][C:27]([C:29]4[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=4)=[C:26]4[C@@H:17]([CH2:18][CH:19]=[C:20]5[C@@H:25]4[CH2:24][CH2:23][CH2:22][CH2:21]5)[C@@H:8]2[CH2:9]3)[CH3:7])[O:4]1.O>O1CCCC1>[CH2:13]1[CH2:12][O:11][C:10]23[O:15][CH2:16][CH2:3][O:4][C:5]2([C@:6]2([CH2:28][C@H:27]([C:29]4[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=4)[C@H:26]4[C@@H:17]([CH2:18][CH:19]=[C:20]5[C@@H:25]4[CH2:24][CH2:23][CH2:22][CH2:21]5)[C@@H:8]2[CH2:9]3)[CH3:7])[O:14]1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 962WaterHCID 3028194Lithium2×HCID 67788990HCID 67788990, compound

Product 1

HCID 86748619HCID 86748619, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

800 ml of ammonia is condensed at -70° C. and mixed with 1.39 g of lithium. After occurrence of the characteristic blue coloring, 18.6 g (40 mmol) of 17,17-bis-(ethylenedioxy)-11-(4-methoxyphenyl)-5,9(11)-estradiene dissolved in 400 ml of tetrahydrofuran is instilled. After 20 more minutes of stirring, the excess lithium is decomposed by the addition of water, the ammonia evaporates, the reaction mixture is poured on saturated ammonium chloride solution and the aqueous phase is extracted with ethyl acetate. The combined organic phases are washed with saturated sodium chloride solution, dried on sodium sulfate and concentrated by evaporation in a vacuum. After chromatography of the crude product on silica gel with a mixture of ethyl acetate/hexane, 15.2 g of 3,3;17,17-bis-(ethylenedioxy)-11β-(4-methoxyphenyl)-5-estrene and 1.4 g of 17,17-bis-(ethylenedioxy)-11-(4-hydroxyphenyl)-5,9(11) -estradiene* are isolated as white foams.

Workup

  1. customcondensed at -70° C.
  2. customthe ammonia evaporates
  3. additionthe reaction mixture is poured on saturated ammonium chloride solution
  4. extractionthe aqueous phase is extracted with ethyl acetate
  5. washThe combined organic phases are washed with saturated sodium chloride solution
  6. customdried on sodium sulfate
  7. concentrationconcentrated by evaporation in a vacuum
  8. additionAfter chromatography of the crude product on silica gel with a mixture of ethyl acetate/hexane, 15.2 g of 3,3

Sources & evidence

ORD record
ord-ba2349e4bdcb4198944ffd7db7d22233
Source dataset
uspto-grants-1995_04
Patent number
US05405979

Reaction notes

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