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

HRID 349949Notes

Reaction equation

HRID 349949 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]=[C:19]([CH2:21]O)[CH:18]=[CH:17][N:16]=1.S(Cl)([Cl:25])=O>>[Cl:25][CH2:21][C:19]1[CH:18]=[CH:17][N:16]=[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:20]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 178613752-(5-Methyl-2-phenyl-4-oxazolylmethoxy)-4-pyridylmethanol

Product 1

HCID 178613044-Chloromethyl-2-(5-methyl-2-phenyl-4-oxazolylmethoxy)pyridineYield 54%

Procedure

A mixture of 2-(5-methyl-2-phenyl-4-oxazolylmethoxy)-4-pyridylmethanol (1.19 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 4-chloromethyl-2-(5-methyl-2-phenyl-4-oxazolylmethoxy)pyridine (680 mg, yield 54%) as colorless crystals from the fraction eluted with ethyl acetate-hexane (1:3, volume ratio). This was recrystallized from ethyl acetate-hexane. Melting point: 104–105° 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-25059e32088b40fdb830d3eb898ddc18
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

Loading…