Reaktion #10452

Reaktionsgleichung

ethyl α-(bromomethyl)acrylate

sodium methoxide

→

title compound

Ausbeute 28.7%

2-Methoxymethylacrylic acid ethyl ester

Ausbeute 28.7%

Lösungsmittel

methanol

methanol

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe suspension is refluxed for 21 hours
2. 2
   Temperaturcooled
3. 3
   Extraktionextracted with dichloromethane
4. 4
   TrocknenThe organic extracts are dried over Na2SO4
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated under vacuum
7. 7
   SonstigeThe resulting residue is purified by flash column chromatography (1:5 ethyl acetate/hexanes)

Vorschrift

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).

Quelle