Thionyl Chloride → Ethyl 6-(chloromethyl)nicotinate

HRID 1030513Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1030513
O[CH2:2][C:3]1[CH:13]=[CH:12][C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][N:4]=1.S(Cl)([Cl:16])=O.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[Cl:16][CH2:2][C:3]1[CH:13]=[CH:12][C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][N:4]=1

Komponenten

5

Edukt 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 15045504Ethyl 6-(hydroxymethyl)pyridine-3-carboxylate

Produkt 1

HCID 15045505Ethyl 6-(chloromethyl)nicotinateAusbeute 90,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 10.5 g of ethyl 6-hydroxymethylnicotinate in chloroform (100 ml) was cooled to 0° C., and 8.28 g of thionyl chloride was added dropwise to the solution. The mixture was stirred at 0° C. for 2 hours, an aqueous solution of sodium hydrogencarbonate was added, and the mixture was extracted with dichloromethane. The organic layer was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, the solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexene/ethyl acetate=6/1) to obtain 10.52 g of ethyl 6-chloromethylnicotinate.

Aufarbeitung

  1. extractionthe mixture was extracted with dichloromethane
  2. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (n-hexene/ethyl acetate=6/1)

Quellen und Nachweise

ORD-Eintrag
ord-c261d04a19c4419686e6e6b2aa1e8fca
Quelldatensatz
uspto-grants-1992_04
Patentnummer
US05106859

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