Thionyl Chloride → 2-(Chloromethyl)-4-methylpyridine

HRID 1693778Notes

Reaction equation

HRID 1693778 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8]O)[CH:3]=1.S(Cl)([Cl:12])=O>C(Cl)Cl>[Cl:12][CH2:8][C:4]1[CH:3]=[C:2]([CH3:1])[CH:7]=[CH:6][N:5]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 12325388(4-Methylpyridin-2-yl)methanol

Product 1

HCID 126752612-(Chloromethyl)-4-methylpyridineYield 72.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture solution of (4-methyl-pyridine-2-yl)-methanol (410 mg, 3.33 mmol) described in Manufacturing Example 11-1-3, thionyl chloride (0.49 mL, 6.66 mmol) and methylene chloride (10 mL) was stirred under reflux for 5 minutes. The reaction solution was allowed to room temperature and concentrated under a reduced pressure. The resulting residue was partitioned into diethyl ether and saturated sodium bicarbonate solution. The organic layer was purified by silica gel column chromatography (ethyl acetate) to obtain the title compound (340 mg, 72.1%).

Workup

  1. temperatureunder reflux for 5 minutes
  2. customwas allowed to room temperature
  3. concentrationconcentrated under a reduced pressure
  4. customThe resulting residue was partitioned into diethyl ether and saturated sodium bicarbonate solution
  5. customThe organic layer was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-22ca8f62d3964d7d9cd4c9edbbc67065
Source dataset
uspto-grants-2012_04
Patent number
US08158657B2

Reaction notes

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