Reacción #10452

Ecuación de reacción

ethyl α-(bromomethyl)acrylate

sodium methoxide

→

title compound

Rendimiento 28.7%

2-Methoxymethylacrylic acid ethyl ester

Rendimiento 28.7%

Disolventes

methanol

methanol

water

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe suspension is refluxed for 21 hours
2. 2
   Temperaturacooled
3. 3
   Extracciónextracted with dichloromethane
4. 4
   SecadoThe organic extracts are dried over Na2SO4
5. 5
   Filtraciónfiltered
6. 6
   Concentraciónconcentrated under vacuum
7. 7
   OtroThe resulting residue is purified by flash column chromatography (1:5 ethyl acetate/hexanes)

Procedimiento

A solution of ethyl α-(bromomethyl)acrylate (0.99 g, 5.1 mmol [Villieras J., Rambaud M., Synthesis, 1982:924–926]) in methanol (10 mL) is added to an ice-cold solution of sodium methoxide (0.33 g, 6.1 mmol) in methanol (50 mL). The suspension is refluxed for 21 hours, cooled, diluted with water and extracted with dichloromethane. The organic extracts are dried over Na2SO4, filtered and concentrated under vacuum. The resulting residue is purified by flash column chromatography (1:5 ethyl acetate/hexanes) to afford the title compound (0.211 g). 1H NMR (200 MHz, CDCl3): δ 6.33–6.26 (m, 1H), 5.88–5.80 (m, 1H), 4.23 (q, 2H), 4.19–4.10 (m, 2H), 3.41 (s, 3H), 1.31 (t, 3H).

Fuente