Ethylene Glycol → 13beta-Ethyl-3-methoxy-6-methyl-17,17-ethylenedioxygona-1,3,5(10),8,14-pentaene

HRID 1077225Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1077225
[CH2:1]([C:3]1([CH2:10][CH2:11][C:12](=O)[CH2:13][CH2:14][CH:15]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19](OC)[CH:18]=2)[CH3:16])[C:7](=O)[CH2:6][CH2:5][C:4]1=O)[CH3:2].[C:26]1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:37]([OH:40])[CH2:38][OH:39].[OH2:41]>C1C=CC=CC=1>[CH2:1]([C@:3]12[CH2:10][CH2:11][C:12]3[C:18]4[CH:19]=[CH:20][C:21]([O:41][CH3:26])=[CH:22][C:17]=4[CH:15]([CH3:16])[CH2:14][C:13]=3[C:7]1=[CH:6][CH2:5][C:4]12[O:40][CH2:37][CH2:38][O:39]1)[CH3:2]

Komponenten

6

Edukt 4

HCID 174Ethylene GlycolHCID 962Water2×HCID 6101p-Toluenesulfonic acidHCID 214854092-Ethyl-2-(6-m-methoxyphenyl-6-methyl-3-oxohexyl)-1,3-cyclopentanedione

Produkt 1

HCID 6814525013beta-Ethyl-3-methoxy-6-methyl-17,17-ethylenedioxygona-1,3,5(10),8,14-pentaene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

Dissolve 2-ethyl-2-(6-m-methoxyphenyl-6-methyl-3-oxohexyl)-1,3-cyclopentanedione (39.7 g) in benzene (500 ml) and reflux with p-toluenesulfonic acid in water (11.0 g). Remove 2 moles of water, add ethyleneglycol (50 ml) and reflux the solution overnight (16 hours). After working up by the usual procedure, filter repeatedly through Florex in hexane. Recrystallize from ethanol to obtain dl-13β-ethyl-3-methoxy-6-methyl-17,17-ethylenedioxygona-1,3,5(10),8,14-pentaene (16.8 g), m.p. 120°-122°; ultraviolet absorption peak at 312 mμ, no infrared absorption in the ketone region.

Aufarbeitung

  1. temperaturereflux the solution overnight (16 hours)
  2. filtrationfilter repeatedly through Florex in hexane
  3. customRecrystallize from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-5a65e9efc80147d2a678da880035a74c
Quelldatensatz
uspto-grants-1976_05
Patentnummer
US03959322

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