Hydrochloric Acid → HCID 19754894, Verbindung

HRID 1588925Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1588925
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:13])[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[C:14]([N:18]([CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1)[C:19](=[O:27])[C:20]1[CH:25]=[CH:24][C:23](Br)=[CH:22][CH:21]=1)([CH3:17])([CH3:16])[CH3:15].Cl>>[CH:28]1([N:18]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:19](=[O:27])[C:20]2[CH:25]=[CH:24][C:23]([O:13][C:5]3[CH:6]=[C:7]([O:11][CH3:12])[C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=3)=[CH:22][CH:21]=2)[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]1

Komponenten

4

Edukt 3

HCID 313Hydrochloric AcidHCID 695053,4,5-TrimethoxyphenolHCID 53933994HCID 53933994, Verbindung

Produkt 1

HCID 19754894HCID 19754894, Verbindung

Versuchsvorschrift

A slurry of cuprous oxide (300 mg, 2.1 mmol) in a solution of 3,4,5-trimethoxyphenol (736 mg, 4.0 mmol) and p-bromobenzoic acid N-tert-butyl-N-cyclohexyl amide (1.35 g, 4.0 mmol) 2,4,6-collidine (20 ml) is refluxed with stirring under a nitrogen atmosphere for 18 hr. The reaction is cooled, poured onto dilute aqueous HCl and extracted three times with ethyl acetate. The combined organic layers are washed twice with saturated aqueous NaCl solution, twice with 5% NaOH solution, twice with saturated NaCl solution and dried (Na2SO4). The drying agent is filtered and the filtrate concentrated in vacuo to give the crude product. This material is chromatographed on silica gel using mixtures of ethyl acetate and hexane as the eluents to give the title compound.

Aufarbeitung

  1. temperatureThe reaction is cooled
  2. extractionextracted three times with ethyl acetate
  3. washThe combined organic layers are washed twice with saturated aqueous NaCl solution, twice with 5% NaOH solution, twice with saturated NaCl solution
  4. dry with materialdried (Na2SO4)
  5. filtrationThe drying agent is filtered
  6. concentrationthe filtrate concentrated in vacuo
  7. customto give the crude product
  8. customThis material is chromatographed on silica gel using mixtures of ethyl acetate and hexane as the eluents

Quellen und Nachweise

ORD-Eintrag
ord-c5883c0685ad47ecbb5f34121a50434d
Quelldatensatz
uspto-grants-1993_06
Patentnummer
US05223539

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