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

HRID 1294140Notes

Reaction equation

HRID 1294140 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[CH:24]=[C:23]([CH2:25]O)[CH:22]=[CH:21][N:20]=1>>[Cl:3][CH2:25][C:23]1[CH:22]=[CH:21][N: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])[CH:24]=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)pyridine

Procedure

To thionyl chloride (4 mL) was added [2-(5-methyl-2-phenyl-4-oxazolylmethoxy)-4-pyridyl]methanol (1.19 g) under ice-cooling, and the mixture was stirred at room temperature for 1 hr. The reaction mixture was concentrated, and saturated aqueous sodium hydrogencarbonate was added to the residue. The mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The obtained residue was subjected to silica gel column chromatography to give crystals of 4-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 needle crystals (0.68 g, 54%). melting point: 104-105° C.

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated
  3. additionsaturated aqueous sodium hydrogencarbonate was added to the residue
  4. extractionThe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-b2cd98da35754a1dad87d13518164979
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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