Dichloromethane → 2-(Chloromethyl)-5-methoxypyridine

HRID 636650

Reaction equation

HRID 636650 reaction equation
O[C:2]1[C:7](C)=[CH:6][C:5]([O:9][CH3:10])=[CH:4][N:3]=1.S(Cl)(Cl)=O.[CH2:15](Cl)[Cl:16]>>[Cl:16][CH2:15][C:2]1[CH:7]=[CH:6][C:5]([O:9][CH3:10])=[CH:4][N:3]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 24386Thionyl ChlorideHCID 178493791HCID 178493791, compound

Product 1

HCID 145171532-(Chloromethyl)-5-methoxypyridine

Procedure

To a solution of 2-hydroxy-methyl-5-methoxy-pyridine (0.68 g, 4.9 mmol) in dry DCM was added dropwise excess thionyl chloride (2.0 mL), and the mixture was refluxed for 2 hours. The solvent was removed in vacuo, and the residue was taken up in EtOAc and washed with NaHCO3 (aq), dried (MgSO4, and concentrated in vacuo. The extremely volatile 2-chloromethyl-5-methoxy-pyridine was obtained as a solution in ethyl acetate to give (984.0 mg, 83.5%) yield.

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. customThe solvent was removed in vacuo
  3. washwashed with NaHCO3 (aq)
  4. dry with materialdried (MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-51e56b89b45d460784ead246e3c0a0e5
Source dataset
uspto-grants-2001_02
Patent number
US06194437B1

Linked notes

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