Sodium Methoxide → Methyl-4-methoxy-5-methoxycarbonyl-nicotinate

HRID 1442898Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1442898
[CH3:1][O:2][C:3](=[O:15])[C:4]1[C:9](Cl)=[C:8]([C:11]([O:13][CH3:14])=[O:12])[CH:7]=[N:6][CH:5]=1.[CH3:16][O-:17].[Na+]>C1COCC1.CO>[CH3:1][O:2][C:3](=[O:15])[C:4]1[C:9]([O:17][CH3:16])=[C:8]([C:11]([O:13][CH3:14])=[O:12])[CH:7]=[N:6][CH:5]=1

Komponenten

5

Edukt 2

HCID 10942334Sodium MethoxideHCID 22019198Dimethyl 4-chloropyridine-3,5-dicarboxylate

Produkt 1

HCID 22019197Methyl-4-methoxy-5-methoxycarbonyl-nicotinate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 6.3 g (27.5 mmol) of methyl-4-chloro-5-methoxycarbonyl-nicotinate in 100 ml of THF is added 6.48 ml (35 mmol) of a 5.4 m solution of sodium methoxide in methanol. The mixture is stirred for 10 minutes and evaporated. 100 ml of a 0.25M aqueous HCl is added to the residue. The solution is made basic with K2CO3 and extracted with ethyl acetate. The organic phase is dried and evaporated to give an oil which crystallised on cooling. There is obtained 6.2 g (quantitative yield) of a solid (M+1=226).

Aufarbeitung

  1. customevaporated
  2. addition100 ml of a 0.25M aqueous HCl is added to the residue
  3. extractionextracted with ethyl acetate
  4. customThe organic phase is dried
  5. customevaporated
  6. customto give an oil which
  7. customcrystallised
  8. temperatureon cooling

Quellen und Nachweise

ORD-Eintrag
ord-046312b3a75d4718a7044456ba304c3d
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07659307B2

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