Sulfuric Acid → Methyl 2-(Dimethoxymethyl)pyridine-5-carboxylate

HRID 346214

Reaktionsgleichung

Reaktionsgleichung von HRID 346214
C([C:3]1[CH:8]=[CH:7][C:6]([C:9]([O:11][CH3:12])=[O:10])=[CH:5][N:4]=1)=O.OS(O)(=O)=O.[CH:18]([O:23][CH3:24])([O:21][CH3:22])OC>CO>[CH3:24][O:23][CH:18]([O:21][CH3:22])[C:3]1[CH:8]=[CH:7][C:6]([C:9]([O:11][CH3:12])=[O:10])=[CH:5][N:4]=1

Komponenten

5

Edukt 3

HCID 1118Sulfuric AcidHCID 9005Trimethyl orthoformateHCID 586269Methyl 6-formylpyridine-3-carboxylate

Produkt 1

HCID 14459972Methyl 2-(Dimethoxymethyl)pyridine-5-carboxylateAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of methyl 2-formylpyridine-5-carboxylate (2.00 g, 12.1 mmol) in methanol (20 ml) and trimethyl orthoformate (5 ml) was added H2SO4 (conc., 1.5 ml). After refluxing overnight, the reaction was cooled and concentrated to a thick slurry and then poured into saturated NaHCO3 (50 ml). The latter was extracted with ether (3×30 ml) and the combined organic layers dried (MgSO4) and concentrated to afford title product (1.91 g, 75%).

Aufarbeitung

  1. temperatureAfter refluxing overnight
  2. temperaturethe reaction was cooled
  3. concentrationconcentrated to a thick slurry
  4. additionpoured into saturated NaHCO3 (50 ml)
  5. extractionThe latter was extracted with ether (3×30 ml)
  6. dry with materialthe combined organic layers dried (MgSO4)
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-5c2b0597d11440a1a0dae16aa413565e
Quelldatensatz
uspto-grants-1991_10
Patentnummer
US05061717

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