Ammonia → 17Alpha-ethyl-3-methoxyestra-1,3,5(10)-trien-17beta-ol

HRID 1077240Notes

Reaction equation

HRID 1077240 reaction equation
[CH2:1]([C@:3]1([OH:23])[CH2:8][CH2:7][C@H:6]2[C:9]3[CH2:10][CH2:11][C:12]4[CH:13]=[C:14]([O:21][CH3:22])[CH:15]=[CH:16][C:17]=4[C:18]=3[CH2:19][CH2:20][C@:4]12[CH3:5])[CH3:2].[Li].N.[Cl-].[NH4+]>O1CCCC1.NC1C=CC=CC=1.O>[CH3:2][CH2:1][C:3]1([OH:23])[C:4]2([CH3:5])[CH2:20][CH2:19][CH:18]3[C:17]4[CH:16]=[CH:15][C:14]([O:21][CH3:22])=[CH:13][C:12]=4[CH2:11][CH2:10][CH:9]3[CH:6]2[CH2:7][CH2:8]1

Participants

8

Reactant 4

HCID 222AmmoniaHCID 25517Ammonium ChlorideHCID 3028194LithiumHCID 6814549517alpha-Ethyl-3-methoxyestra-1,3,5(10),8-tetraen-17-ol

Product 1

HCID 8658417Alpha-ethyl-3-methoxyestra-1,3,5(10)-trien-17beta-olYield 66.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6115AnilineSolventHCID 8028TetrahydrofuranSolvent

Procedure

Add dl-17α-ethyl-3-methoxyestra-1,3,5(10),8-tetraen-17-ol (3 g) in tetrahydrofuran (50 ml) to lithium (0.8 g) in aniline (8 ml) and liquid ammonia (200 ml). Stir for two hours, decompose by adding ammonium chloride and water, and extract with ether. Wash, dry and evaporate the organic extract, and crystallize from ethyl acetate-hexane to obtain dl-17α-ethyl-3-methoxyestra-1,3,5(10)-trien-17β-ol (2 g), m.p. 133°--135°; ultraviolet absorption maximum at 279 mμ (ε2,120).

Workup

  1. extractionextract with ether
  2. washWash
  3. customdry
  4. customevaporate the organic extract
  5. customcrystallize from ethyl acetate-hexane

Sources & evidence

ORD record
ord-7412800590ff40b5ab273d6d6729b4da
Source dataset
uspto-grants-1976_05
Patent number
US03959322

Reaction notes

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