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

HRID 77820

Reaction equation

HRID 77820 reaction equation
[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

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 707366-Methyl-2-pyridylmethanol

Product 1

HCID 765462-(Chloromethyl)-6-methylpyridineYield 85.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-78e6bd01107849bd8231580d44d84968
Source dataset
uspto-grants-2014_09
Patent number
US08841327B2

Linked notes

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