Thionyl Chloride → 2-Chloromethyl-3,4-dimethoxypyridinium chloride

HRID 1801442Notes

Reaction equation

HRID 1801442 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH2:11]O)=[N:5][CH:6]=[CH:7][C:8]=1[O:9][CH3:10].S(Cl)([Cl:15])=O>>[ClH:15].[Cl:15][CH2:11][C:4]1[C:3]([O:2][CH3:1])=[C:8]([O:9][CH3:10])[CH:7]=[CH:6][N:5]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 107258093,4-Dimethoxy-2-pyridinemethanol

Product 1

HCID 162169282-Chloromethyl-3,4-dimethoxypyridinium chlorideYield 85%

Procedure

A solution of (3,4-dimethoxypyridin-2-yl)methanol (1 g, 5.91 mmol) in CH2CH2 (11.82 mL) was treated dropwise with thionyl chloride (1 mL, 13.70 mmol) with stirring at room temperature. The reaction mixture was stirred for 2 h, and then concentrated directly in vacuo. The resulting residue was washed with 3×10 mL Et2O, the resulting solids collected by filtration, and then dried under reduced pressure to afford the title compound as a white solid (1.12 g, 85%), which was used in the subsequent step without further purification. Data for 1-1: LC/MS: rt=0.58 min, m/z (M+H)=188.09 found; 188.04 required. 3,4-dimethoxy-2-{[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]methyl}-pyridine (1-2)

Workup

  1. stirringThe reaction mixture was stirred for 2 h
  2. concentrationconcentrated directly in vacuo
  3. washThe resulting residue was washed with 3×10 mL Et2O
  4. filtrationthe resulting solids collected by filtration
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-f14e89ff1cc347a1842561e72e041be1
Source dataset
uspto-grants-2013_01
Patent number
US08349830B2

Reaction notes

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