2-Chloropyridine → Pyriproxyfen

Participants

Reaction Steps

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.

Provenance & Evidence