Thionyl Chloride → 2-(Chloromethyl)-4-(3-methoxypropoxy)-3-methylpyridine

HRID 727901Notes

Reaction equation

HRID 727901 reaction equation
O[CH2:2][C:3]1[C:8]([CH3:9])=[C:7]([O:10][CH2:11][CH2:12][CH2:13][O:14][CH3:15])[CH:6]=[CH:5][N:4]=1.S(Cl)([Cl:18])=O>ClCCl>[Cl:18][CH2:2][C:3]1[C:8]([CH3:9])=[C:7]([O:10][CH2:11][CH2:12][CH2:13][O:14][CH3:15])[CH:6]=[CH:5][N:4]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 104657494-(3-Methoxypropoxy)-3-methyl-2-pyridinemethanol

Product 1

HCID 110316672-(Chloromethyl)-4-(3-methoxypropoxy)-3-methylpyridineYield 96.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

450 mg of the 2-hydroxymethyl-4-(3-methoxypropoxy)-3-methylpyridine prepared above was dissolved in 20 ml of dichloromethane to obtain a solution. 760 mg of thionyl chloride was dropwise added to this solution at 0° C. The obtained mixture was stirred at a room temperature for 2 hours. After the completion of the reaction, the reaction mixture was distilled to remove the dichloromethane and the thionyl chloride. A saturated aqueous solution of sodium hydrogencarbonate was added to the obtained residue. The obtained mixture was extracted with chloroform. The obtained chloroform layer was concentrated to obtain 470 mg of 2-chloromethyl-4-(3-methoxypropoxy)-3-methylpyridine as a brown crystal.

Workup

  1. customto obtain a solution
  2. customAfter the completion of the reaction
  3. distillationthe reaction mixture was distilled
  4. customto remove the dichloromethane
  5. additionA saturated aqueous solution of sodium hydrogencarbonate was added to the obtained residue
  6. extractionThe obtained mixture was extracted with chloroform
  7. concentrationThe obtained chloroform layer was concentrated

Sources & evidence

ORD record
ord-b16dcae3737b4d52b5d56a784fdc85f4
Source dataset
uspto-grants-1991_09
Patent number
US05045552

Reaction notes

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