Ammonia → 3-Methoxyestra-2,5(10)-dien-17beta-ol

HRID 1077214Notes

Reaction equation

HRID 1077214 reaction equation
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:18]2[C@@H:17]3[C@H:8]([C@H:9]4[C@@:13]([CH2:15][CH2:16]3)([CH3:14])[C@@H:12]([OH:21])[CH2:11][CH2:10]4)[CH2:7][CH2:6][C:5]=2[CH:4]=1.[Li].N.[Cl-].[NH4+]>O1CCCC1.O.C(O)C>[CH3:1][O:2][C:3]1[CH2:4][C:5]2[CH2:6][CH2:7][C@@H:8]3[C@@H:17]([C:18]=2[CH2:19][CH:20]=1)[CH2:16][CH2:15][C@@:13]1([CH3:14])[C@H:9]3[CH2:10][CH2:11][C@@H:12]1[OH:21]

Participants

8

Reactant 4

HCID 222AmmoniaHCID 25517Ammonium ChlorideHCID 246206Estradiol 3-methyl etherHCID 3028194Lithium

Product 1

HCID 1019633-Methoxyestra-2,5(10)-dien-17beta-olYield 64.2%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Add dl-3-methoxyestra-1,3,5(10)-trien-17β-ol (1.3 g) in tetrahydrofuran (40 ml) to a stirred solution of lithium (1.3 g) in liquid ammonia (100 ml). After 15 minutes add ethanol (20 ml) dropwise and when the blue color is discharged add ammonium chloride and water and extract the mixture with ether. Wash, dry and evaporate the ethereal solution and recrystallize the residue from ethanol-hexane to obtain dl-3-methoxyestra-2,5(10)-dien-17β-ol (0.84 g), m.p. 120-123°; infrared absorption maxima at 3.25 μ, 5.8 μ, 6 μ.

Workup

  1. extractionextract the mixture with ether
  2. washWash
  3. customdry
  4. customevaporate the ethereal solution
  5. customrecrystallize the residue from ethanol-hexane

Sources & evidence

ORD record
ord-f388ce3e178d4d83ac4255bc30913c7e
Source dataset
uspto-grants-1976_05
Patent number
US03959322

Reaction notes

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