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

HRID 1415034

Reaction equation

HRID 1415034 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-af236d2dc2e74c6a90062a74e8f1b137
Source dataset
uspto-grants-1977_01
Patent number
US04002746

Linked notes

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