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

HRID 1294116Notes

Reaction equation

HRID 1294116 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21]O)=[CH:17][N:16]=1.C1(C)C=CC=CC=1.S(Cl)([Cl:32])=O>O>[Cl:32][CH2:21][C:18]1[CH:19]=[CH:20][C:15]([O:14][CH2:13][C:3]2[N:4]=[C:5]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)[O:6][C:2]=2[CH3:1])=[N:16][CH:17]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 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 962WaterSolvent

Procedure

To a mixture of 2-(5-methyl-2-phenyl-4-oxazolylmethoxy)pyridine-5-methanol (12.2 g) and toluene (200 ml) was added thionyl chloride (5.39 g), and the mixture was stirred at room temperature for 1 hr. Iced water was added to the reaction mixture, and after neutralization with saturated aqueous sodium hydrogencarbonate, the mixture 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 give crystals (11.7 g, yield 90%) of 5-chloromethyl-2-(5-methyl-2-phenyl-4-oxazolylmethoxy)pyridine from a fraction eluted with ethyl acetate-hexane (1:3, v/v). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 86-87° C.

Workup

  1. extractionafter neutralization with saturated aqueous sodium hydrogencarbonate, the mixture was 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-e3bc104c7d774e47b5c51e64b160b754
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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