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

HRID 49222Notes

Reaction equation

HRID 49222 reaction equation
O=S(Cl)[Cl:3].[CH3:5][O:6][C:7]1[CH:12]=[C:11]([CH2:13]O)[CH:10]=[CH:9][N:8]=1>C(Cl)(Cl)Cl>[CH3:5][O:6][C:7]1[CH:12]=[C:11]([CH2:13][Cl:3])[CH:10]=[CH:9][N:8]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 14462410(2-Methoxypyridin-4-yl)methanol

Product 1

HCID 179484394-(Chloromethyl)-2-methoxypyridine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

1.57 ml (21.6 mmol) of SOCl2 are added dropwise, whilst cooling with ice and under a N2 atmosphere, to a solution of 1.5 g (10.8 mmol) of 2-methoxy-4-(hydroxymethyl)-pyridine [for preparation see J. Org. Chem. 54 (1989), 5580] in 13 ml of chloroform. After 16 h at RT, the mixture is concentrated by evaporation, water and 2N sodium hydroxide solution are added to the residue, and extraction immediately takes place 3 times with chloroform. The organic phases are washed with water and brine, dried (Na2SO4) and concentrated by evaporation to form 2-methoxy-pyridin-4-yl-methylchloride; 1H NMR (CDCl3) δ8.15 (d, 1H), 6.90 (d, 1H), 6.76 (s, 1H), 4.49 (s, 2H), 3.94 (s, H3C).

Workup

  1. concentrationthe mixture is concentrated by evaporation, water and 2N sodium hydroxide solution
  2. additionare added to the residue, and extraction immediately takes place 3 times with chloroform
  3. washThe organic phases are washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-398ea0ab4f274ddfb4bf56f80c405661
Source dataset
uspto-grants-2004_03
Patent number
US06706731B2

Reaction notes

Loading…