2-Chloropyridine → Pyriproxyfen

A mixture of 1-methyl-2-(4-phenoxyphenoxy)ethanol (2.0 g, 8.2 mmol), 2-chloropyridine (4.0 g, 35 mmol), flaked 95% sodium hydroxide (1 g, 24 mmol) and tetra-n-butylammonium bromide (0.13 g) was stirred 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 (5 g) twice. The hydrochloric acid layer was washed with toluene (10 g). A 10% aqueous sodium hydroxide solution was added thereto to make the mixture sufficiently basic. The basic mixture was further extracted with toluene (10 g) twice, and the toluene layer was washed with a 10% aqueous sodium hydroxide solution and a saturated aqueous sodium chloride solution in order and dried over anhydrous magnesium sulfate. After removal of the solvent, the residue was purified by silica gel column chromatography to give 2-[1-methyl- 2-(4-phenoxyphenoxy)ethoxy]pyridine (1.87 g) as white crystals.

1. temperatureto cool
2. washthe resultant mixture was washed with water
3. extractionextracted with 35% hydrochloric acid (5 g) twice
4. washThe hydrochloric acid layer was washed with toluene (10 g)
5. additionA 10% aqueous sodium hydroxide solution was added
6. extractionThe basic mixture was further extracted with toluene (10 g) twice
7. washthe toluene layer was washed with a 10% aqueous sodium hydroxide solution
8. dry with materiala saturated aqueous sodium chloride solution in order and dried over anhydrous magnesium sulfate
9. customAfter removal of the solvent
10. customthe residue was purified by silica gel column chromatography

ORD-Eintrag

ord-9478d0c3a3944225adf0b02b98f51785

Quelldatensatz

uspto-grants-1990_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US04970222