3-Hydroxypyridine → HCID 19082034, compound

HRID 53216Notes

Reaction equation

HRID 53216 reaction equation
[H-].[Na+].O[C:4]1[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=1.[CH3:10][C:11]1[O:15][N:14]=[C:13]([C:16]2[CH:26]=[C:25]([CH3:27])[C:19]([O:20][CH2:21][CH2:22][CH2:23]I)=[C:18]([CH3:28])[CH:17]=2)[N:12]=1>CN(C=O)C>[CH3:10][C:11]1[O:15][N:14]=[C:13]([C:16]2[CH:26]=[C:25]([CH3:27])[C:19]([O:20][CH2:21][CH2:22][CH2:23][C:4]3[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=3)=[C:18]([CH3:28])[CH:17]=2)[N:12]=1

Participants

5

Reactant 3

HCID 79713-HydroxypyridineHCID 24758Sodium hydrideHCID 53951419HCID 53951419, compound

Product 1

HCID 19082034HCID 19082034, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of sodium hydride (70 mg, 2.8 mmol) and 3-hydroxypyridine (0.24 g, 2.56 mmol) in DMF was added dropwise 1 g (1 g, 2.8 mmol) of 4-(5-methyl-1,2,4-oxadiazol-3-yl)-2,6-dimethylphenoxypropyl iodide in DMF, and the mixture was stirred at room temperature for 2 days. The mixture was washed with water, extracted with ethyl acetate, and the organic layer was washed with water and dried over magnesium sulfate. The dry organic layer was concentrated in vacuo, passed through a pad of silica gel eluting with hexane/ethyl acetate (1:1) to afford 0.48 g (55.1%) of 3-[3-[4-(5-methyl-1,2,4-oxadiazol-3-yl)-2,6-dimethylphenoxy]propyl]-pyridine, as an oil, which crystallized on standing in ether, m.p. 46°-49° C.

Workup

  1. washThe mixture was washed with water
  2. extractionextracted with ethyl acetate
  3. washthe organic layer was washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationThe dry organic layer was concentrated in vacuo

Sources & evidence

ORD record
ord-512b452ee58b4a1e8f4b712f863ac6bb
Source dataset
uspto-grants-1997_04
Patent number
US05618821

Reaction notes

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