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Sodium ethoxide → Ethyl 2-ethoxycarbonyl-5-(4-ethoxycarbonylphenoxy)pentanoate

HRID 2268483
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2268483
[O-:1][CH2:2][CH3:3].[Na+].[C:5]([O:11][CH2:12][CH3:13])(=[O:10])[CH2:6][C:7]([O-:9])=O.I[CH2:15][CH2:16][CH2:17][O:18][C:19]1[CH:29]=[CH:28][C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:21][CH:20]=1>C(O)C.O>[CH2:2]([O:1][C:7]([CH:6]([CH2:15][CH2:16][CH2:17][O:18][C:19]1[CH:29]=[CH:28][C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:21][CH:20]=1)[C:5]([O:11][CH2:12][CH3:13])=[O:10])=[O:9])[CH3:3]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 2723922Sodium ethoxideHCID 3595298Propanedioic acid, monoethyl esterHCID 18348598Ethyl 4-(3-iodopropoxy)benzoate

Produkt 1

HCID 18348516Ethyl 2-ethoxycarbonyl-5-(4-ethoxycarbonylphenoxy)pentanoateAusbeute 47,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittel
HCID 962
Water
Lösungsmittel

Versuchsvorschrift

To a solution of sodium ethoxide (90%, 6.79 g) in ethanol (250 ml) was dropwise added ethyl malonate (12.0 g) with cooling with ice. The reaction mixture was allowed to warm to room temperature and stirred for 30 min and ethyl 4-(3-iodopropoxy)benzoate (25.0 g) was dropwise added with cooling with ice. The reaction mixture was allowed to warm to room temperature and stirred for 12 hr. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride and dried. The solvent was removed in vacuo. The residue was purified by silica gel column chromatography (hexane to hexane:ethyl acetate=10:1) to yield the entitled compound (13.0 g) as an oil.

Aufarbeitung

  1. temperaturewith cooling with ice
  2. temperaturewith cooling with ice
  3. temperatureto warm to room temperature
  4. stirringstirred for 12 hr
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with water and saturated aqueous sodium chloride
  7. customdried
  8. customThe solvent was removed in vacuo
  9. customThe residue was purified by silica gel column chromatography (hexane to hexane:ethyl acetate=10:1)

Quellen und Nachweise

ORD-Eintrag
ord-cfa28ac0c36c4948a5eb142ec90c6d39
Quelldatensatz
uspto-grants-2001_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06326369B1

Notizen zur Reaktion

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