Methanesulfonic Acid → 1-(4-Pyridyl)-2,3-bis(methoxycarbonyl)-6,7-dimethoxynaphthalene

HRID 1743035

Reaktionsgleichung

Reaktionsgleichung von HRID 1743035
CO[CH:3](OC)[C:4]1[C:9]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)=[CH:8][C:7]([O:16][CH3:17])=[C:6]([O:18][CH3:19])[C:5]=1CO.[C:24]([O:32][CH3:33])(=[O:31])/[CH:25]=[CH:26]\[C:27]([O:29][CH3:30])=[O:28].[CH3:34]S(O)(=O)=O>C(O)(=O)C.C1(C)C=CC=CC=1>[N:13]1[CH:12]=[CH:11][C:10]([C:9]2[C:4]3[C:3](=[CH:8][C:7]([O:16][CH3:17])=[C:6]([O:18][CH3:19])[CH:5]=3)[CH:34]=[C:26]([C:27]([O:29][CH3:30])=[O:28])[C:25]=2[C:24]([O:32][CH3:33])=[O:31])=[CH:15][CH:14]=1

Komponenten

6

Edukt 3

HCID 6395Methanesulfonic AcidHCID 5271565Dimethyl maleateHCID 220073783,4-Dimethoxy-6-(4-pyridyl) hydroxymethylbenzaldehyde dimethylacetal

Produkt 1

HCID 117286421-(4-Pyridyl)-2,3-bis(methoxycarbonyl)-6,7-dimethoxynaphthaleneAusbeute 62,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a solution of 3,4-dimethoxy-6-(4-pyridyl) hydroxymethylbenzaldehyde dimethylacetal (18.4 g) in a mixture of acetic acid (50 ml) and toluene (50 ml) is added dimethyl maleate (8.64 ml), and the mixture is refluxed for one hour. To the mixture is added methanesulfonic acid (9.33 ml), and the mixture is refluxed for 8 hours while removing the resulting water with a Dean-Stalk apparatus. The mixture is cooled to room temperature, and concentrated. The residue is dissolved in chloroform, and the pH value thereof is adjusted with aqueous potassium carbonate solution to pH 8. The mixture is extracted twice with each 100 ml of chloroform, and the extracts are washed with a saturated sodium chloride solution, dried over magnesium sulfate, and concentrated. The resulting residue is crystallized from diethyl ether to give a diester compound, 1-(4-pyridyl)-2,3-bis(methoxycarbonyl)-6,7-dimethoxynaphthalene (13.5 g).

Aufarbeitung

  1. temperaturethe mixture is refluxed for one hour
  2. temperaturethe mixture is refluxed for 8 hours
  3. customwhile removing the resulting water with a Dean-Stalk apparatus
  4. concentrationconcentrated
  5. dissolutionThe residue is dissolved in chloroform
  6. extractionThe mixture is extracted twice with each 100 ml of chloroform
  7. washthe extracts are washed with a saturated sodium chloride solution
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated
  10. customThe resulting residue is crystallized from diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-ea6e579a5bde40b8844841c48e68995a
Quelldatensatz
uspto-grants-1994_08
Patentnummer
US05342941

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