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

HRID 77825Notes

Reaction equation

HRID 77825 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-cc8b8aa7ab2d4b3da69f5d8ea9ee125c
Source dataset
uspto-grants-2014_09
Patent number
US08841327B2

Reaction notes

Loading…