Thionyl Chloride → 5-Chloromethyl-2-(5-methyl-2-phenyl-4-oxazolyl)methoxypyridine

HRID 349982Notes

Reaction equation

HRID 349982 reaction equation
S(Cl)([Cl:3])=O.[CH3:5][C:6]1[O:10][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:8][C:7]=1[CH2:17][O:18][C:19]1[N:24]=[CH:23][C:22]([CH2:25]O)=[CH:21][CH:20]=1.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[Cl:3][CH2:25][C:22]1[CH:21]=[CH:20][C:19]([O:18][CH2:17][C:7]2[N:8]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[O:10][C:6]=2[CH3:5])=[N:24][CH:23]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 178328032-(5-Methyl-2-phenyl-4-oxazolylmethoxy)pyridine-5-methanol

Product 1

HCID 178328085-Chloromethyl-2-(5-methyl-2-phenyl-4-oxazolyl)methoxypyridineYield 90.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Thionyl chloride (5.39 g) was added to a mixture of 6-(5-methyl-2-phenyl-4-oxazolylmethoxy)-3-pyridylmethanol (12.2 g) and toluene (200 ml), which was stirred at room temperature for 1 hour. Ice water was added to the reaction mixture, which was neutralized with saturated aqueous sodium bicarbonate solution, and was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 5-chloromethyl-2-(5-methyl-2-phenyl-4-oxazolylmethoxy)pyridine (11.7 g, yield 90%) as colorless crystals from the fraction eluted with ethyl acetate-hexane (1:3, volume ratio). This was recrystallized from ethyl acetate-hexane to obtain colorless prism crystals. Melting point: 86–87° C.

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9af92987d832474197664dbd89c76871
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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