Reaction #10452

Reaction equation

ethyl α-(bromomethyl)acrylate

sodium methoxide

→

title compound

Yield 28.7%

2-Methoxymethylacrylic acid ethyl ester

Yield 28.7%

Solvents

methanol

methanol

water

Conditions

Workup

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

Procedure

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