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

HRID 911427Notes

Reaction equation

HRID 911427 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-23398c82509c4a15a1845e2115bfdfa2
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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