Thionyl Chloride → 5-Chloromethyl-2-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]pyridine

HRID 1295239Notes

Reaction equation

HRID 1295239 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][C:8]([CH3:21])=[C:9]([CH2:11][O:12][C:13]2[N:18]=[CH:17][C:16]([CH2:19]O)=[CH:15][CH:14]=2)[N:10]=1.S(Cl)([Cl:24])=O>>[Cl:24][CH2:19][C:16]1[CH:15]=[CH:14][C:13]([O:12][CH2:11][C:9]2[N:10]=[C:6]([C:2]3[O:1][CH:5]=[CH:4][CH:3]=3)[O:7][C:8]=2[CH3:21])=[N:18][CH:17]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 688864106-[2-(2-Furyl)-5-methyl-4-oxazolylmethoxy]-3-pyridylmethanol

Product 1

HCID 230763795-Chloromethyl-2-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]pyridineYield 71%

Procedure

A mixture of 6-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]-3-pyridylmethanol (1.87 g) and thionyl chloride (15 ml) was stirred at room temperature for 1 hr. After concentration under reduced pressure, ice water was added to the residue. The mixture was neutralized with saturated aqueous sodium hydrogen carbonate and 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, and 5-chloromethyl-2-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]pyridine (1.41 g, yield 71%) 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: 95–96° C.

Workup

  1. concentrationAfter concentration under reduced pressure, ice water
  2. additionwas added to the residue
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-fe5660f4d6944e82bf093bea57af1c75
Source dataset
uspto-grants-2007_07
Patent number
US07241785B2

Reaction notes

Loading…