Реакция #10452

Уравнение реакции

ethyl α-(bromomethyl)acrylate

sodium methoxide

→

title compound

Выход 28.7%

2-Methoxymethylacrylic acid ethyl ester

Выход 28.7%

Растворители

methanol

methanol

water

Условия реакции

Обработка

1. 1
   ТемператураThe suspension is refluxed for 21 hours
2. 2
   Температураcooled
3. 3
   Экстракцияextracted with dichloromethane
4. 4
   СушкаThe organic extracts are dried over Na2SO4
5. 5
   Фильтрацияfiltered
6. 6
   Концентрированиеconcentrated under vacuum
7. 7
   ДругоеThe resulting residue is purified by flash column chromatography (1:5 ethyl acetate/hexanes)

Методика

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).

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