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

HRID 10356

反応式

HRID 10356 の反応式
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]

参加物

5

反応物 2

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

生成物 1

HCID 20770134Ethyl 2-(methoxymethyl)prop-2-enoate収率 28.7%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒2 回HCID 962Water溶媒

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).

後処理

  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)

出典と根拠

ORDレコード
ord-bda05e49b0404071a41e804aec975155
出典データセット
uspto-grants-2006_08
特許番号
US07094780B1

関連ノート

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