Thionyl Chloride → 2-(Chloromethyl)-6-methylpyridine

HRID 2041310Notes

Reaction equation

HRID 2041310 reaction equation
S(Cl)([Cl:3])=O.O[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH3:13])[N:8]=1>C(Cl)Cl>[Cl:3][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH3:13])[N:8]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 707366-Methyl-2-pyridylmethanol

Product 1

HCID 765462-(Chloromethyl)-6-methylpyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Add with stirring a solution of thionyl chloride (0.77 mL, 10.6 mmol) in dry DCM (20 mL) to 2-hydroxymethyl-6-methylpyridine (1.0 g, 8.12 mmol) in dry DCM (20 mL) at 0° C. Continue stirring at 0° C. for 1.25 h. Quench with isopropanol and concentrate in vacuo. Dissolve the residue in DCM, wash with saturated aqueous NaHCO3, dry over anhydrous Na2SO4, and concentrate in vacuo to give the title compound. MS (ES+) m/z 142 (M+H)+.

Workup

  1. additionAdd
  2. customQuench with isopropanol
  3. concentrationconcentrate in vacuo
  4. dissolutionDissolve the residue in DCM
  5. washwash with saturated aqueous NaHCO3
  6. dry with materialdry over anhydrous Na2SO4
  7. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-f1c18235263b4be7a6719bbc0be2d3f0
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

Loading…