Thionyl Chloride → 3-Chloromethyl-5-(5-methyl-2-phenyl-4-oxazolylmethoxy)pyridine

HRID 349952Notes

Reaction equation

HRID 349952 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:16]=[C:17]([CH2:21]O)[CH:18]=[N:19][CH:20]=1.S(Cl)([Cl:25])=O>>[Cl:25][CH2:21][C:17]1[CH:18]=[N: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])[CH:16]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 178612255-(5-Methyl-2-phenyl-4-oxazolylmethoxy)-3-pyridylmethanol

Product 1

HCID 230249673-Chloromethyl-5-(5-methyl-2-phenyl-4-oxazolylmethoxy)pyridineYield 64%

Procedure

A mixture of 5-(5-methyl-2-phenyl-4-oxazolylmethoxy)-3-pyridylmethanol (1.33 g) and thionyl chloride (4 ml) was stirred at room temperature for 1 hour. After the reaction mixture was concentrated, saturated aqueous sodium bicarbonate solution was added to the mixture, which was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4), and concentrated. The residue was subjected to silica gel column chromatography to obtain 3-chloromethyl-5-(5-methyl-2-phenyl-4-oxazolylmethoxy)pyridine (911 mg, yield 64%) as colorless crystals from the fraction eluted with tetrahydrofuran-hexane (1:1, volume ratio). This was recrystallized from tetrahydrofuran-hexane. Melting point: 98–99° C.

Workup

  1. concentrationAfter the reaction mixture was concentrated
  2. additionsaturated aqueous sodium bicarbonate solution was added to the mixture, which
  3. extractionwas extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1f4d81cfbfcb40afb7fe4fb8316618ed
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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