Hydrochloric Acid → 1-(3-Methoxypyridin-4-yl)ethan-1-one

HRID 2309805Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2309805
[Na].CO[C:4](=[O:13])[C:5]1[CH:10]=[CH:9][N:8]=[CH:7][C:6]=1[O:11][CH3:12].[C:14](OC)(=O)C.Cl.C(=O)(O)[O-].[Na+]>O.CO>[CH3:12][O:11][C:6]1[CH:7]=[N:8][CH:9]=[CH:10][C:5]=1[C:4](=[O:13])[CH3:14]

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 6584Methyl AcetateHCID 516892Sodium BicarbonateHCID 5360545Sodium2×HCID 11400991Methyl 3-methoxyisonicotinate

Produkt 1

HCID 128039871-(3-Methoxypyridin-4-yl)ethan-1-oneAusbeute 46,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittel2×HCID 962WaterLösungsmittel

Versuchsvorschrift

A dry 50 mL three neck flask fitted with a reflux condenser and internal thermometer was charged with dry methanol (20 mL). Sodium (516 mg, 0.022 mol) was added in portions and after all the sodium had dissolved the methanol was removed by distillation. The resulting sodium methoxide was cooled and a mixture of methyl-3-methoxyisonicotinoate (2.50 g, 0.015 mol) and methyl acetate (6.65 g, 0.090 mol) was added dropwise. The mixture was refluxed for four hours, allowed to cool and dissolved in water (9.0 mL) and concentrated hydrochloric acid (6.0 mL). The resulting mixture was heated to reflux for 2.5 hours, cooled, and basified with 5% sodium bicarbonate. The mixture was extracted with chloroform (4×50 mL) and the combined extracts dried over sodium sulfate, concentrated, and chromatographed through a short column of silica gel to afford 3-methoxy-4-acetylpyridine (1.05 g, 46%). mp. 36°-37° C.

Aufarbeitung

  1. customwas removed by distillation
  2. temperatureThe resulting sodium methoxide was cooled
  3. additionwas added dropwise
  4. temperatureThe mixture was refluxed for four hours
  5. temperatureto cool
  6. temperatureThe resulting mixture was heated
  7. temperatureto reflux for 2.5 hours
  8. temperaturecooled
  9. extractionThe mixture was extracted with chloroform (4×50 mL)
  10. dry with materialthe combined extracts dried over sodium sulfate
  11. concentrationconcentrated
  12. customchromatographed through a short column of silica gel

Quellen und Nachweise

ORD-Eintrag
ord-e3cdeeb5afc740cfb4792bbd8e833c57
Quelldatensatz
uspto-grants-1987_09
Patentnummer
US04697012

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