Thionyl Chloride → 5-(Chloromethyl)-2-methylpyridine

HRID 629458Notes

Reaction equation

HRID 629458 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8]O)=[CH:4][CH:3]=1.S(Cl)([Cl:12])=O>C1COCC1.O.C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>[Cl:12][CH2:8][C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[N:7][CH:6]=1

Participants

7

Reactant 2

HCID 24386Thionyl ChlorideHCID 11228788(6-Methylpyridin-3-yl)methanol

Product 1

HCID 122143385-(Chloromethyl)-2-methylpyridineYield 65.2%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of (6-methylpyridin-3-yl)methanol (1.08 g) in THF (15.0 mL) was added thionyl chloride (1.57 g) under ice-cooling, and the mixture was stirred overnight at room temperature. The reaction mixture was diluted with water and ethyl acetate, saturated aqueous sodium bicarbonate was added thereto, and the mixture was partitioned. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (0.81 g).

Workup

  1. temperaturecooling
  2. additionwas added
  3. customthe mixture was partitioned
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-72124e27cf3d477883c3a99edb724c25
Source dataset
uspto-grants-2016_04
Patent number
US09315458B2

Reaction notes

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