Potassium Carbonate → Methyl 6-(chloromethyl)pyridine-2-carboxylate

HRID 876550

Reaktionsgleichung

Reaktionsgleichung von HRID 876550
O=S(Cl)[Cl:3].O[CH2:6][C:7]1[N:12]=[C:11]([C:13]([O:15][CH3:16])=[O:14])[CH:10]=[CH:9][CH:8]=1.C([O-])([O-])=O.[K+].[K+]>ClCCl>[Cl:3][CH2:6][C:7]1[N:12]=[C:11]([C:13]([O:15][CH3:16])=[O:14])[CH:10]=[CH:9][CH:8]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 24386Thionyl ChlorideHCID 11513809Methyl 6-(hydroxymethyl)picolinate

Produkt 1

HCID 53404482Methyl 6-(chloromethyl)pyridine-2-carboxylateAusbeute 101,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

SOCl2 (57 g, 0.48 mol) was added to a solution of methyl 6-(hydroxymethyl)picolinate 70 (40.0 g, 0.239 mol) (Chem. Eur. J. 2006, 12, 6393-6402) in dichloromethane (500 mL) at room temperature. The mixture was stirred at 40° C. for 1 h and sat. aq K2CO3 was added to adjust the pH to 9. The mixture was extracted with CH2Cl2 and the combined organics were washed with brine, dried (Na2SO4), and concentrated in vacuo to give 71 (45 g).

Aufarbeitung

  1. extractionThe mixture was extracted with CH2Cl2
  2. washthe combined organics were washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e824456de4934b2790428962505f9a09
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08987258B2

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