2-(Bromomethyl)acrylic acid ethyl ester → Ethyl 2-(methoxymethyl)prop-2-enoate

HRID 10356

반응식

HRID 10356 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

반응물 2

HCID 3106202-(Bromomethyl)acrylic acid ethyl esterHCID 10942334Sodium Methoxide

생성물 1

HCID 20770134Ethyl 2-(methoxymethyl)prop-2-enoate수율 28.7%

시약·촉매·용매 2

HCID 887Methanol용매2회HCID 962Water용매

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

  1. temperatureThe suspension is refluxed for 21 hours
  2. temperaturecooled
  3. extractionextracted with dichloromethane
  4. dry with materialThe organic extracts are dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. 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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