Reacción #357304

Ecuación de reacción

methyl 5-chloro-2-hydroxy-4-[(4-methoxybenzyl)oxy]benzoate

(2S)-oxiran-2-ylmethyl 3-nitrobenzenesulfonate

caesium carbonate

→

titled compound

Rendimiento 74.0%

Methyl 5-chloro-4-[(4-methoxybenzyl)oxy]-2-[(2S)-oxiran-2-ylmethoxy]benzoate

Rendimiento 74.0%

Disolventes

dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe mixture was partitioned between water and ethyl acetate
2. 2
   Lavadothe organic phase was washed twice with water and once with brine
3. 3
   Concentraciónfinally concentrated
4. 4
   OtroThe crude material was purified by flash chromatoghrphy on silica gel (eluent:ethyl acetate/n-heptane)

Procedimiento

A solution of methyl 5-chloro-2-hydroxy-4-[(4-methoxybenzyl)oxy]benzoate (0.37 g, 1.16 mmol), (2S)-oxiran-2-ylmethyl 3-nitrobenzenesulfonate (0.30 g, 1.16 mmol) and caesium carbonate (0.45 g, 1.4 mmol) in dimethylformamide (15 mL) was stirred at room temperature overnight. The mixture was partitioned between water and ethyl acetate, and the organic phase was washed twice with water and once with brine, and finally concentrated. The crude material was purified by flash chromatoghrphy on silica gel (eluent:ethyl acetate/n-heptane), yielding the titled compound (0.33, 74%).

Fuente