Ethyl 2-methylacetoacetate → Diethyl 2-acetyl-2-methyloctanedioate

HRID 230719Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 230719
[CH3:1][CH:2]([C:8]([CH3:10])=[O:9])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[O-][CH2:12]C.[Na+].BrC[CH2:17][CH2:18][CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22]>C(O)C>[C:21]([CH2:20][CH2:19][CH2:18][CH2:17][CH2:1][C:2]([CH3:12])([C:8]([CH3:10])=[O:9])[C:3]([O:5][CH2:6][CH3:7])=[O:4])([O:23][CH2:24][CH3:25])=[O:22]

Komponenten

5

Edukt 3

HCID 701Ethyl 2-methylacetoacetateHCID 117544Ethyl 6-bromohexanoateHCID 2723922Sodium ethoxide

Produkt 1

HCID 22266834Diethyl 2-acetyl-2-methyloctanedioate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Versuchsvorschrift

A mixture of 25 g of ethyl 2-methylacetoacetate, 64 mL of a 21% sodium ethoxide solution in ethanol and 34 mL of ethyl 6-bromohexanoate is refluxed in 200 mL of ethanol overnight. The mixture is filtered and solvent is evaporated. The residue is partitioned between 1 M HCl and chloroform. The organic layer is dried over magnesium sulfate and purified on silica gel using 1:10 ethyl acetate/hexanes as eluant to yield 22 g of ethyl 2-(5-carbethoxypentyl)-2-methylacetoacetate.

Aufarbeitung

  1. filtrationThe mixture is filtered
  2. customsolvent is evaporated
  3. customThe residue is partitioned between 1 M HCl and chloroform
  4. dry with materialThe organic layer is dried over magnesium sulfate
  5. custompurified on silica gel using 1:10 ethyl acetate/hexanes as eluant

Quellen und Nachweise

ORD-Eintrag
ord-17ef86e880474e19993e2715feb71bc5
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07566790B2

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