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

HRID 226223Notes

Reaction equation

HRID 226223 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>C1(C)C=CC=CC=1>[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 112.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-Hydroxymethyl-4-(3-methoxypropoxy)-3-methylpyridine (5.0 g (23.7 mmol)) was dissolved in toluene (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 (6.13 g (yield: 97.3%)).

Workup

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

Sources & evidence

ORD record
ord-d7ec685598ca42bda094384dbddfc0c8
Source dataset
uspto-grants-2009_07
Patent number
US07557217B2

Reaction notes

Loading…