Sodium hydride → 2-[2-(4-Phenoxyphenoxy)ethoxy]pyridine

HRID 1073512Notes

Reaction equation

HRID 1073512 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1.[H][H].[O:12]([C:19]1[CH:28]=[CH:27][C:22]([O:23][CH2:24][CH2:25]Br)=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CN(C)C=O.O>[O:12]([C:19]1[CH:20]=[CH:21][C:22]([O:23][CH2:24][CH2:25][O:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=2)=[CH:27][CH:28]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 132544871-(2-Bromoethoxy)-4-phenoxybenzeneHCID 178418361HCID 178418361, compoundHCID 178516071HCID 178516071, compound

Product 1

HCID 99485052-[2-(4-Phenoxyphenoxy)ethoxy]pyridineYield 28.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent3×

Procedure

To a suspension of sodium hydride (132 mg, 3.3 mmol; 60% in oil) in dimethylformamide (5 ml), a solution of 2-hydroxypyridine (314 mg, 3.3 mmol) in dimethylformamide (3 ml) was dropwise added with stirring, and stirring was continued at room temperature until the generation of hydrogen gas ceased. To the resultant solution, there was dropwise added a solution of 2-(4-phenoxyphenoxy)ethyl bromide (879 mg, 3.0 mmol) in dimethylformamide (3ml), and the mixture was stirred at room temperature overnight. The reaction mixture was poured into water (70 ml) and extracted with toluene (25 ml) three times. The toluene layer was dried over anhydrous magnesium sulfate, and the solvent was removed by evaporation. The residue was purified by silica gel column chromatography to give 2-[2-(4-phenoxyphenoxy)ethoxy]pyridine (264 mg) as white crystals. M.P., 94.2° C.

Workup

  1. stirringstirring
  2. stirringthe mixture was stirred at room temperature overnight
  3. extractionextracted with toluene (25 ml) three times
  4. dry with materialThe toluene layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was removed by evaporation
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-db7d9561cbf241008eee6465d7e36808
Source dataset
uspto-grants-1990_11
Patent number
US04970222

Reaction notes

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