2-Chloropyridine → Pyriproxyfen

HRID 1073513Notes

Reaction equation

HRID 1073513 reaction equation
[H-].[Na+].[CH3:3][CH:4]([OH:20])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:9][CH:8]=1.[H][H].Cl[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=1>CN(C)C=O.O>[CH3:3][CH:4]([O:20][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=1)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 79772-ChloropyridineHCID 24758Sodium hydrideHCID 103995681-(4-Phenoxyphenoxy)propan-2-olHCID 178418361HCID 178418361, compound

Product 1

HCID 91753PyriproxyfenYield 79%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of sodium hydride (200 mg, 5.0 mmol; 60% in oil) in dimethylformamide (5 ml), a solution of 1-methyl-2-(4-phenoxyphenoxy)ethanol (1.22 g, 5.0 mmol) in dimethylformamide (3 ml) was dropwise added with stirring, and the mixture was kept at an inner temperature of 50° to 60° C. until the generation of hydrogen gas ceased. 2-Chloropyridine (684 mg, 6.0 mmol) was dropwise added thereto, followed by stirring at 100° to 110° C. for 5 hours. The reaction mixture was cooled to room temperature, poured into water (100 ml) and extracted with toluene (40 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-[1-methyl-2-(4-phenoxyphenoxy)ethoxy] pyridine (1.27 g) as pale yellow liquid. nD20.5 1.5823. Upon being allowed to stand for a few days, the liquid solidified to give crystals. M.P., 49.7° C.

Workup

  1. stirringby stirring at 100° to 110° C. for 5 hours
  2. extractionextracted with toluene (40 ml) three times
  3. dry with materialThe toluene layer was dried over anhydrous magnesium sulfate
  4. customthe solvent was removed by evaporation
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-38987a05ccc84a4cbc15b28bb1829721
Source dataset
uspto-grants-1990_11
Patent number
US04970222

Reaction notes

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