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

HRID 1295229Notes

Reaction equation

HRID 1295229 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 hr. The reaction mixture was concentrated and saturated aqueous sodium hydrogen carbonate was added. The mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and 4-chloromethyl-2-(5-methyl-2-phenyl-4-oxazolylmethoxy)pyridine (680 mg, yield 54%) was obtained as colorless crystals from a fraction eluted with ethyl acetate-hexane (1:3, volume ratio). The crystals were recrystallized from ethyl acetate-hexane. melting point: 104–105° C.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionsaturated aqueous sodium hydrogen carbonate was added
  3. extractionThe mixture was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with saturated brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-10547356df3249c9809a02531e12ebc3
Source dataset
uspto-grants-2007_07
Patent number
US07241785B2

Reaction notes

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