反应详情

A mixture of 2-hydroxy-6-trifluoromethylpyridine (2.0 g, 12.3 mmol), sodium hydroxide (0.52 g, 12.9 mmol) and 15-crown-5 (1 drop) in dry toluene (25 ml) were stirred at reflux for 2 hours. The toluene was removed under reduced pressure and the white salt residue was dissolved in dry DMF (15 ml). Methyl 2-chloromethylphenylacetate (2.44 g, 12.3 mmol) in dry DMF (15 ml) was added dropwise along with sodium iodide (10 mg). The mixture was stirred at 75° C. for 2 hours, poured into water and extracted with diethyl ether. The ether extracts were washed with water, dried and the ether removed in vacuo leaving an oil which was purified by column chromatography (silica eluted with 10% ethyl acetate in hexane) to give methyl 2-(6-tri-fluoromethylpyrid-2-yloxymethyl)phenylacetate (3.3 g, 83%) (Compound No.5 in Table 1) as a yellow oil; 1H NMR (270 MHz)δ: 3.68(3H,s), 3.84(2H,s), 5.46(2H,s), 6.89(1H,d), 7,20-7.70(6H,m) ppm.

1. temperatureat reflux for 2 hours
2. customThe toluene was removed under reduced pressure
3. dissolutionthe white salt residue was dissolved in dry DMF (15 ml)
4. stirringThe mixture was stirred at 75° C. for 2 hours
5. extractionextracted with diethyl ether
6. washThe ether extracts were washed with water
7. customdried
8. customthe ether removed in vacuo
9. customleaving an oil which
10. customwas purified by column chromatography (silica eluted with 10% ethyl acetate in hexane)