Acetamidomalonic acid diethyl ester → diethyl (E)-2-acetamido-2-(2-butenyl)malonate

HRID 362150

反応式

HRID 362150 の反応式
[Na].[C:2]([NH:5][CH:6]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:7]([O:9][CH2:10][CH3:11])=[O:8])(=[O:4])[CH3:3].Br[CH2:18]/[CH:19]=[CH:20]/[CH3:21]>C(O)C>[C:2]([NH:5][C:6]([CH2:18]/[CH:19]=[CH:20]/[CH3:21])([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:7]([O:9][CH2:10][CH3:11])=[O:8])(=[O:4])[CH3:3]

参加物

5

反応物 3

HCID 14041Acetamidomalonic acid diethyl esterHCID 6375322-Butene, 1-bromo-, (2E)-HCID 5360545Sodium

生成物 1

HCID 86753714diethyl (E)-2-acetamido-2-(2-butenyl)malonate収率 87.8%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

3.86 g (168 mmol) of sodium metal were dissolved in 106 ml of anhydrousethanol. 36.35 g (168 mmol) of diethyl acetamidomalonate dissolved in 225 ml of anhydrous ethanol were added and the mixture was heated under refluxfor 10 minutes. 22.66 g (168 mmol) of (E)-1-bromo-2-butene were added dropwise at room temperature and the mixture was stirred overnight and then evaporated to dryness under a vacuum. The residue was partitioned between ethyl acetate and 0.1M hydrochloric acid. The organic phase was washed with saturated sodium hydrogen carbonate solution and then with saturated sodium chloride solution and dried over anhydrous magnesium sulphate. The solvent was evaporated to give 40 g of diethyl (E)-2-acetamido-2-(2-butenyl)malonate as a colourless oil; 1H NMR (250 MHz, CDCl3) δ: 1.25 (t, 6 H), 1.6 (d, 3 H), 2.0 (s, 3 H), 2.9 (d, 2 H), 4.2 (q, 4 H), 5.15 (m, 1 H) 5.5 (m, 1 H), 6.7 s, 1 H).

後処理

  1. additionwere added
  2. temperaturethe mixture was heated under refluxfor 10 minutes
  3. customevaporated to dryness under a vacuum
  4. customThe residue was partitioned between ethyl acetate and 0.1M hydrochloric acid
  5. washThe organic phase was washed with saturated sodium hydrogen carbonate solution
  6. dry with materialwith saturated sodium chloride solution and dried over anhydrous magnesium sulphate
  7. customThe solvent was evaporated

出典と根拠

ORDレコード
ord-d0b36201542649e09c8e188c5f1a57f7
出典データセット
uspto-grants-1999_02
特許番号
US05866684

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