2-Chloropyridine → Pyriproxyfen

HRID 579946

Reaktionsgleichung

Reaktionsgleichung von HRID 579946
[H-].[Na+].Cl[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1.[CH3:10][CH:11]([OH:27])[CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:16][CH:15]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH3:10][CH:11]([O:27][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1)[CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:16][CH:15]=1

Komponenten

6

Edukt 3

HCID 79772-Chloropyridine2×HCID 24758Sodium hydrideHCID 103995681-(4-Phenoxyphenoxy)propan-2-ol

Produkt 1

HCID 91753PyriproxyfenAusbeute 121,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a mixture of sodium hydride (0.61 g, 15 mmol; 60% in oil) and 2-chloropyridine (1 g, 9 mmol), there was dropwise added a mixture of 1-methyl-2-(4-phenoxyphenoxy)ethanol (3.0 g, 12 mmol) and 2-chloropyridine (5 g, 44 mmol) with stirring at an inner temperature of 0° to 5° C. Tetra-n-butylammonium bromide (0.2 g) was added to the resultant mixture, and stirring was continued at room temperature for 40 minutes and at an inner temperature of 85° to 90° C. for 6 hours. After allowed to cool, toluene (10 g) was added thereto, and the resultant mixture was washed with water and extracted with 35% hydrochloric acid (7.5 g) twice. To the hydrochloric acid layer, a 10% aqueous sodium hydroxide solution was added to make basic, followed by extraction with toluene (10 g) twice. The toluene extract was washed with a 10% aqueous sodium hydroxide solution and a saturated aqueous sodium chloride solution in order and dried over anhydrous magnesium sulfate. Removal of the solvent gave 2-[1-methyl-2-(4-phenoxyphenoxy)ethoxy]pyridine (3.51 g) as pale brown crystals.

Aufarbeitung

  1. additionwas dropwise added
  2. stirringstirring
  3. temperatureto cool
  4. washthe resultant mixture was washed with water
  5. extractionextracted with 35% hydrochloric acid (7.5 g) twice
  6. additionTo the hydrochloric acid layer, a 10% aqueous sodium hydroxide solution was added
  7. extractionfollowed by extraction with toluene (10 g) twice
  8. extractionThe toluene extract
  9. washwas washed with a 10% aqueous sodium hydroxide solution
  10. dry with materiala saturated aqueous sodium chloride solution in order and dried over anhydrous magnesium sulfate
  11. customRemoval of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-3255a421512846b4b7003989083fce7e
Quelldatensatz
uspto-grants-1988_06
Patentnummer
US04751225

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