تفاعل #10452

معادلة التفاعل

ethyl α-(bromomethyl)acrylate

sodium methoxide

→

title compound

المردود 28.7%

2-Methoxymethylacrylic acid ethyl ester

المردود 28.7%

المذيبات

methanol

methanol

water

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe suspension is refluxed for 21 hours
2. 2
   درجة الحرارةcooled
3. 3
   استخلاصextracted with dichloromethane
4. 4
   تجفيفThe organic extracts are dried over Na2SO4
5. 5
   ترشيحfiltered
6. 6
   تركيزconcentrated under vacuum
7. 7
   أخرىThe resulting residue is purified by flash column chromatography (1:5 ethyl acetate/hexanes)

الإجراء التجريبي

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).

المصدر