2-(Bromomethyl)acrylic acid ethyl ester → Ethyl 2-(methoxymethyl)prop-2-enoate
반응식
Br[CH2:2][C:3](=[CH2:9])[C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH3:10][O-:11].[Na+]>CO.O>[CH2:7]([O:6][C:4](=[O:5])[C:3]([CH2:2][O:11][CH3:10])=[CH2:9])[CH3:8]참가 물질
5
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).
후처리
- temperatureThe suspension is refluxed for 21 hours
- temperaturecooled
- extractionextracted with dichloromethane
- dry with materialThe organic extracts are dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated under vacuum
- customThe resulting residue is purified by flash column chromatography (1:5 ethyl acetate/hexanes)
출처 및 근거
- ORD 기록
- ord-bda05e49b0404071a41e804aec975155
- 출처 데이터셋
- uspto-grants-2006_08
- 특허 번호
- US07094780B1
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