Ammonia → Estradiol 3-methyl ether

HRID 1077213

Reaktionsgleichung

Reaktionsgleichung von HRID 1077213
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:18]2[C:17]3[CH2:16][CH2:15][C@@:13]4([CH3:14])[C@@H:9]([CH2:10][CH2:11][C@@H:12]4[OH:21])[C:8]=3[CH2:7][CH2:6][C:5]=2[CH:4]=1.N.NC1C=CC=CC=1.[Li].[Cl-].[NH4+]>O1CCCC1.O>[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

Komponenten

8

Edukt 5

HCID 222AmmoniaHCID 6115AnilineHCID 25517Ammonium ChlorideHCID 3028194LithiumHCID 110552063-Methoxyestra-1,3,5(10),8-tetraen-17beta-ol

Produkt 1

HCID 246206Estradiol 3-methyl etherAusbeute 31,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Add dl-3-methoxyestra-1,3,5(10),8-tetraen-17β-ol (37.5 g) in tetrahydrofuran (350 ml) to a stirred solution of liquid ammonia (1 liter) and aniline (45 ml). Add lithium (2 g), stir for 30 minutes, and then add ammonium chloride (20 g) followed by water. Extract with ether-benzene (1:1) and wash the organic solution with water, excess 3N hydrochloric acid, water and dry. Evaporate the solvent and recrystallize the residue from ethyl acetate-hexane to obtain dl-3-methoxyestra-1,3,5(10)-trien-17β-ol (12 g), m.p. 121-124°; ultraviolet absorption peak at 278 mμ (ε1,810); infrared maxima at 3.0 μ, 6.2 μ, 6.75 μ.

Aufarbeitung

  1. extractionExtract with ether-benzene (1:1)
  2. washwash the organic solution with water, excess 3N hydrochloric acid, water
  3. customdry
  4. customEvaporate the solvent
  5. customrecrystallize the residue from ethyl acetate-hexane

Quellen und Nachweise

ORD-Eintrag
ord-d4b607b6e1e14a5dbe63e47e523ca206
Quelldatensatz
uspto-grants-1976_05
Patentnummer
US03959322

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