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Ethyl bromoacetate → Diethyl 2-prop-1-yl-2-ethoxycarbonylsuccinate

HRID 1788638
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1788638
[CH2:1]([CH:4]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:2][CH3:3].[H-].[Na+].Br[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]>CN(C)C=O.O>[CH2:1]([C:4]([C:10]([O:12][CH2:13][CH3:14])=[O:11])([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:2][CH3:3]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 7748Ethyl bromoacetateHCID 16552Diethyl propylmalonateHCID 24758Sodium hydride

Produkt 1

HCID 20075591Diethyl 2-prop-1-yl-2-ethoxycarbonylsuccinateAusbeute 97,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel
HCID 6228
Dimethylformamide
Lösungsmittel

Versuchsvorschrift

Diethyl prop-1-ylmalonate (70.23 g) was added dropwise to a stirred suspension of sodium hydride (8.35 g) in dimethylformamide (400 ml) under an atmosphere of nitrogen at 10° to 15° C. Following the addition, the mixture was allowed to stir at room temperature until effervescence ceased. The resulting clear solution was cooled again and ethyl bromoacetate (58.06 g) was added. The mixture was heated at 70° C. for 2 hours then allowed to cool, diluted with water, and extracted with ether. The extracts were washed with water, dried over magnesium sulphate, and concentrated to give almost pure diethyl 2-prop-1-yl-2-ethoxycarbonylsuccinate (97.35 g, 97%) as a pale yellow liquid.

Aufarbeitung

  1. additionthe addition
  2. temperatureThe resulting clear solution was cooled again
  3. temperatureThe mixture was heated at 70° C. for 2 hours
  4. temperatureto cool
  5. extractionextracted with ether
  6. washThe extracts were washed with water
  7. dry with materialdried over magnesium sulphate
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-dc9ee49832794fa68de60f9cd2a0a860
Quelldatensatz
uspto-grants-1987_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04684396

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