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

HRID 349984Notes

Reaction equation

HRID 349984 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-hour. The reaction mixture was concentrated under reduced pressure, and saturated aqueous sodium bicarbonate solution was added to the residue, 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 5-chloromethyl-2-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]pyridine (1.41 g, yield 71%) as colorless crystals from the fraction eluted with ethyl acetate-hexane (1:3, volume ratio). This was recrystallized from ethyl acetate-hexane. Melting point: 95–96° C.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and saturated aqueous sodium bicarbonate solution
  2. additionwas added to the residue, 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-cc742caac6784d4cae0ded54bce123d7
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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