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

HRID 850893

Reaktionsgleichung

Reaktionsgleichung von HRID 850893
[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]

Komponenten

5

Edukt 3

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

Produkt 1

HCID 86753714diethyl (E)-2-acetamido-2-(2-butenyl)malonateAusbeute 87,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Versuchsvorschrift

3.86 g (168 mmol) of sodium metal were dissolved in 106 ml of anhydrous ethanol. 36.35 g (168 mmol) of diethyl acetamidomalonate dissolved in 225 ml of anhydrous ethanol were added and the mixture was heated under reflux for 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) d: 1.25 (t, 6H), 1.6 (d, 3H), 2.0 (s, 3H), 2.9 (d, 2H), 4.2 (q, 4H), 5.15 (m, 1H) 5.5 (m, 1H), 6.7 s, 1H).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-b1230e009ad84b1b907ce581c0b71474
Quelldatensatz
uspto-grants-2000_01
Patentnummer
US06018020

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