Dimethylformamide → HCID 17861255, compound

HRID 349987Notes

Reaction equation

HRID 349987 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:8])=[N:6][CH:7]=1.Cl[CH2:10][C:11]1[N:12]=[C:13]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[O:14][C:15]=1[CH3:16].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH3:8][C:5]1[CH:4]=[CH:3][C:2]([O:1][CH2:10][C:11]2[N:12]=[C:13]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[O:14][C:15]=2[CH3:16])=[CH:7][N:6]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 142752-Methyl-5-hydroxypyridineHCID 97942894-(Chloromethyl)-5-methyl-2-phenyl-1,3-oxazole

Product 1

HCID 17861255HCID 17861255, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 5-hydroxy-2-methylpyridine (8.46 g), 4-chloromethyl-5-methyl-2-phenyloxazole (15.20 g), potassium carbonate (15.98 g) and N,N-dimethylformamide (200 ml) was stirred at 80° C. for 3 hours, poured into water, and 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 2-methyl-5-(5-methyl-2-phenyl-4-oxazolylmethoxy)pyridine (19.68 g, yield 96%) as pale yellow crystals from the fraction eluted with tetrahydrofuran-hexane (1:1, volume ratio). This was recrystallized from acetone-hexane. Melting point: 103–104° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f77a12b6a8294becafe5b106df362780
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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