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

HRID 226224Notes

Reaction equation

HRID 226224 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>C(OCC)(=O)C>[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 112.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-Hydroxymethyl-4-(3-methoxypropoxy)-3-methylpyridine (5.0 g (23.7 mmol)) was dissolved in ethyl acetate (40 ml), and thionyl chloride (4.23 g (35.6 mmol)) was added dropwise into the solution in a temperature that did not exceed 25° C. Stirring was carried out at room temperature, and then after it had been confirmed by TLC that the starting material had disappeared, vacuum concentration was carried out, thus obtaining 2-chloromethyl-4-(3-methoxypropoxy)-3-methylpyridine (6.14 g (yield: 97.4%)).

Workup

  1. customdid not exceed 25° C
  2. customwas carried out at room temperature
  3. concentrationvacuum concentration

Sources & evidence

ORD record
ord-139da017e5424f6c99f23ac86da1a6f5
Source dataset
uspto-grants-2009_07
Patent number
US07557217B2

Reaction notes

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