Acetamidomalonic acid diethyl ester → Diethyl 2-acetylamino-2-(4-methyl-4-nitropentyl)malonate

HRID 432992Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 432992
[O-]CC.[Na+].[C:5]([NH:8][CH:9]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:10]([O:12][CH2:13][CH3:14])=[O:11])(=[O:7])[CH3:6].[CH3:20][C:21]([N+:27]([O-:29])=[O:28])([CH3:26])[CH2:22][CH2:23][CH2:24]I>C(O)C>[C:5]([NH:8][C:9]([CH2:24][CH2:23][CH2:22][C:21]([CH3:26])([N+:27]([O-:29])=[O:28])[CH3:20])([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:10]([O:12][CH2:13][CH3:14])=[O:11])(=[O:7])[CH3:6]

Komponenten

5

Edukt 3

HCID 14041Acetamidomalonic acid diethyl esterHCID 2723922Sodium ethoxideHCID 99430631-Iodo-4-methyl-4-nitro-pentane

Produkt 1

HCID 9968068Diethyl 2-acetylamino-2-(4-methyl-4-nitropentyl)malonateAusbeute 83,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Versuchsvorschrift

20% Sodium ethoxide (3.74 g, 11 mmol) and diethyl 2-acetamidomalonate (2.39 g, 11 mmol) were dissolved in ethanol (10 ml). A solution of 4-methyl-4-nitropentyl iodide (2.57 g, 10 mmol) in ethanol (8 ml) was added and the mixture was refluxed under heating for 5 h. Ethanol was evaporated by concentration under reduced pressure and ethyl acetate (50 ml) was added. The mixture was washed with water (20 ml) and saturated brine (20 ml). Ethyl acetate was evaporated by concentration under reduced pressure and the residue was purified by silica gel column chromatography to give the objective compound (2.89 g, yield 83.4%).

Aufarbeitung

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 5 h
  3. customEthanol was evaporated by concentration under reduced pressure and ethyl acetate (50 ml)
  4. additionwas added
  5. washThe mixture was washed with water (20 ml) and saturated brine (20 ml)
  6. customEthyl acetate was evaporated by concentration under reduced pressure
  7. customthe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-17ca81093ca44bfaab46202d2c4bf367
Quelldatensatz
uspto-grants-2003_12
Patentnummer
US06664412B2

Notizen zur Reaktion

Wird geladen…