反応 #10452

反応方程式

ethyl α-(bromomethyl)acrylate

sodium methoxide

→

title compound

収率 28.7%

2-Methoxymethylacrylic acid ethyl ester

収率 28.7%

溶媒

methanol

methanol

water

反応条件

後処理

1. 1
   温度The suspension is refluxed for 21 hours
2. 2
   温度cooled
3. 3
   抽出extracted with dichloromethane
4. 4
   乾燥The organic extracts are dried over Na2SO4
5. 5
   ろ過filtered
6. 6
   濃縮concentrated under vacuum
7. 7
   その他The resulting residue is purified by flash column chromatography (1:5 ethyl acetate/hexanes)

実験手順

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).

出典