Réaction #10452

Équation de réaction

ethyl α-(bromomethyl)acrylate

sodium methoxide

→

title compound

Rendement 28.7%

2-Methoxymethylacrylic acid ethyl ester

Rendement 28.7%

Solvants

methanol

methanol

water

Conditions de réaction

Traitement

1. 1
   TempératureThe suspension is refluxed for 21 hours
2. 2
   Températurecooled
3. 3
   Extractionextracted with dichloromethane
4. 4
   SéchageThe organic extracts are dried over Na2SO4
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated under vacuum
7. 7
   AutreThe resulting residue is purified by flash column chromatography (1:5 ethyl acetate/hexanes)

Mode opératoire

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).

Source