Thionyl Chloride → Ethyl 6-(chloromethyl)pyridine-2-carboxylate

HRID 2356616

Reaktionsgleichung

Reaktionsgleichung von HRID 2356616
S(Cl)([Cl:3])=O.O[CH2:6][C:7]1[N:12]=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:10]=[CH:9][CH:8]=1>>[Cl:3][CH2:6][C:7]1[N:12]=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:10]=[CH:9][CH:8]=1

Komponenten

3

Edukt 2

HCID 24386Thionyl ChlorideHCID 109211412-Pyridinecarboxylic acid, 6-(hydroxymethyl)-, ethyl ester

Produkt 1

HCID 15614003Ethyl 6-(chloromethyl)pyridine-2-carboxylate

Reaktionsbedingungen

Temperatur
12.5 °C

Versuchsvorschrift

Thionyl chloride (13.8 ml) was added over ˜15 minutes to a stirred solution of ethyl 6-(hydroxymethyl)-2-pyridinecarboxylate (28.5 g) in MDC (200 ml) maintaining the temperature at 10-15° C. using an ice-water bath. On completion of the addition the mixture was stirred at room temperature for 1 hour. The solvent was evaporated and the residue partitioned between toluene (200 ml)/saturated bicarb (sodium bicarbonate solution, 200 ml). The layers were separated and the organic phase washed with water (150 ml). The solvent was evaporated to leave a pale oil which solidified on standing. (31.3 g).

Aufarbeitung

  1. additionOn completion of the addition the mixture
  2. customThe solvent was evaporated
  3. customthe residue partitioned between toluene (200 ml)/saturated bicarb (sodium bicarbonate solution, 200 ml)
  4. customThe layers were separated
  5. washthe organic phase washed with water (150 ml)
  6. customThe solvent was evaporated
  7. customto leave a pale oil which

Quellen und Nachweise

ORD-Eintrag
ord-1df03204a7da44a6b0d601d75004ba84
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07759369B2

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