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

HRID 1415060Notes

Reaction equation

HRID 1415060 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 2 hours, decompose by adding ammonium chloride and water, and extract with ether. Wash, dry and evaporate the organic extract, and crystallize from ethyl acetatehexane 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 acetatehexane

Sources & evidence

ORD record
ord-f2e43891741845679833540267732568
Source dataset
uspto-grants-1977_01
Patent number
US04002746

Reaction notes

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