Thionyl Chloride → 2-(Chloromethyl)-6-methylpyridine

HRID 77820

Reaktionsgleichung

Reaktionsgleichung von HRID 77820
[CH3:1][C:2]1[N:7]=[C:6]([CH2:8]O)[CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:12])=O>C(Cl)Cl>[Cl:12][CH2:8][C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[N:7]=1

Komponenten

4

Edukt 2

HCID 24386Thionyl ChlorideHCID 707366-Methyl-2-pyridylmethanol

Produkt 1

HCID 765462-(Chloromethyl)-6-methylpyridineAusbeute 85,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of (6-methyl-pyridin-2-yl)-methanol (1.44 g, 11.7 mmol), thionyl chloride (1.45 mL, 19.9 mmol) and methylene chloride (20 mL) was stirred under reflux for 40 minutes. The reaction solution was cooled to room temperature and then concentrated under a reduced pressure. The residue was partitioned into sodium bicarbonate solution and diethyl ether. The organic layer was concentrated under a reduced pressure, and the residue was purified by silica gel chromatography (ethyl acetate) to obtain the title compound (1.42 g, 85.8%).

Aufarbeitung

  1. temperatureunder reflux for 40 minutes
  2. concentrationconcentrated under a reduced pressure
  3. customThe residue was partitioned into sodium bicarbonate solution and diethyl ether
  4. concentrationThe organic layer was concentrated under a reduced pressure
  5. customthe residue was purified by silica gel chromatography (ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-78e6bd01107849bd8231580d44d84968
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841327B2

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