반응 #10452

반응 방정식

ethyl α-(bromomethyl)acrylate

sodium methoxide

→

title compound

수율 28.7%

2-Methoxymethylacrylic acid ethyl ester

수율 28.7%

용매

methanol

methanol

water

반응 조건

후처리

1. 1
   온도The suspension is refluxed for 21 hours
2. 2
   온도cooled
3. 3
   추출extracted with dichloromethane
4. 4
   건조The organic extracts are dried over Na2SO4
5. 5
   여과filtered
6. 6
   농축concentrated under vacuum
7. 7
   기타The resulting residue is purified by flash column chromatography (1:5 ethyl acetate/hexanes)

실험 절차

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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