Hydrochloric Acid → 13-Ethylgon-4-ene-3,17-dione

HRID 1415008

Reaktionsgleichung

Reaktionsgleichung von HRID 1415008
[CH2:1]([C@:3]12[CH2:11][CH2:10][C@@H:9]3[C:12]4[CH2:13][CH:14]=[C:15]([O:20]C)[CH2:16][C:17]=4[CH2:18][CH2:19][C@H:8]3[C@@H:7]1[CH2:6][CH2:5][C:4]2=[O:22])[CH3:2].CO.Cl.C(=O)(O)[O-].[Na+]>O>[CH2:1]([C@:3]12[CH2:11][CH2:10][C@@H:9]3[C@@H:12]4[C:17]([CH2:18][CH2:19][C@H:8]3[C@@H:7]1[CH2:6][CH2:5][C:4]2=[O:22])=[CH:16][C:15](=[O:20])[CH2:14][CH2:13]4)[CH3:2]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 102242MethoxygonadieneHCID 516892Sodium Bicarbonate

Produkt 1

HCID 1037926413-Ethylgon-4-ene-3,17-dioneAusbeute 81,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Add 13β-ethyl-3-methoxy-gona-2,5(10)-dien-17-one (12.9 g.) with stirring under nitrogen to methanol (300 cc.) containing 11N hydrochloric acid (20 cc) and water (13 cc.). Stir two hours and add sodium bicarbonate (21 g.) portionwise. Filter the mixture and evaporate the filtrate to dryness. Recrystallize the residue from ethyl acetate (75 cc.) to obtain the title compound (10 g.), m.p. 158-161° C; ultraviolet absorption peak at 240 mμ (ε17,800); infrared absorption peaks at 5.78, 6.00, 6.17 μ.

Aufarbeitung

  1. filtrationFilter the mixture
  2. customevaporate the filtrate to dryness
  3. customRecrystallize the residue from ethyl acetate (75 cc.)

Quellen und Nachweise

ORD-Eintrag
ord-5a9a8694484c474a9f90165bb63ebbf4
Quelldatensatz
uspto-grants-1977_01
Patentnummer
US04002746

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