Thionyl Chloride → 3-(chloromethyl)-2-ethylPyridine

HRID 1686Notes

Reaction equation

HRID 1686 reaction equation
[CH2:1]([C:3]1[C:8]([CH2:9]O)=[CH:7][CH:6]=[CH:5][N:4]=1)[CH3:2].S(Cl)([Cl:13])=O>C(Cl)Cl>[CH2:1]([C:3]1[C:8]([CH2:9][Cl:13])=[CH:7][CH:6]=[CH:5][N:4]=1)[CH3:2]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 19690951(2-Ethylpyridin-3-yl)methanol

Product 1

HCID 196909583-(chloromethyl)-2-ethylPyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

The 2-ethyl-3-hydroxymethylpyridine (2.3 g, 16.8 mmol) was dissolved in CH2Cl2 (100 mL) and cooled under nitrogen to 0° C. and thionyl chloride (7.0 mL) was slowly added and the reaction was stirred for 3 hours. The solvent was removed under reduced pressure and the residue was partitioned between CH2Cl2 (100 mL) and saturated aqueous sodium bicarbonate (100 mL). The organic layer was dried with MgSO4, filtered, and the solvent removed under reduced pressure to give the desired 2-ethyl-3-chloromethylpyridine.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was partitioned between CH2Cl2 (100 mL) and saturated aqueous sodium bicarbonate (100 mL)
  3. dry with materialThe organic layer was dried with MgSO4
  4. filtrationfiltered
  5. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-090d23f63738479ca8c99ffd51c34f39
Source dataset
uspto-grants-1998_03
Patent number
US05726172

Reaction notes

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