2-(4-Bromo-2,6-dimethyl-phenyl)-5-(cyclohexyl-hydroxy-methyl)-3-methoxy-cyclopent-2-enone → 2-(4-bromo-2,6-dimethyl-phenyl)-4-[1-cyclohexyl-meth-(E)-ylidene]-cyclopentane-1,3-dione

HRID 1631882Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1631882
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9]2[C:10](=[O:24])[CH:11]([CH:16]([CH:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)O)[CH2:12][C:13]=2[O:14]C)=[C:4]([CH3:25])[CH:3]=1>C(O)C.Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH3:25])[C:5]([CH:9]2[C:10](=[O:24])/[C:11](=[CH:16]/[CH:18]3[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]3)/[CH2:12][C:13]2=[O:14])=[C:6]([CH3:8])[CH:7]=1

Komponenten

4

Edukt 1

HCID 668685772-(4-Bromo-2,6-dimethyl-phenyl)-5-(cyclohexyl-hydroxy-methyl)-3-methoxy-cyclopent-2-enone

Produkt 1

HCID 668680902-(4-bromo-2,6-dimethyl-phenyl)-4-[1-cyclohexyl-meth-(E)-ylidene]-cyclopentane-1,3-dioneAusbeute 19,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 2-(4-bromo-2,6-dimethyl-phenyl)-5-(cyclohexyl-hydroxy-methyl)-3-methoxy-cyclopent-2-enone (1.38 g, 3.4 mmol) in ethanol (27.6 ml) and 2N aqueous hydrochloric acid (13.8 ml) is subjected to microwave irradiation at 130° C. for 40 minutes. The reaction mixture is concentrated under vacuum to remove ethanol. The aqueous layer was extracted with ethyl acetate (3×100 ml) and combined organic layers are dried with sodium sulfate and concentrated under vacuum to obtain crude mass. The compound was purified by column chromatography to give 2-(4-bromo-2,6-dimethyl-phenyl)-4-[1-cyclohexyl-meth-(E)-ylidene]-cyclopentane-1,3-dione (250 mg).

Aufarbeitung

  1. customirradiation at 130° C. for 40 minutes
  2. concentrationThe reaction mixture is concentrated under vacuum
  3. customto remove ethanol
  4. extractionThe aqueous layer was extracted with ethyl acetate (3×100 ml)
  5. dry with materialare dried with sodium sulfate
  6. concentrationconcentrated under vacuum
  7. customto obtain crude mass
  8. customThe compound was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-6f236b47e799460bb81928685550b6b1
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08791303B2

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