Diethyl Malonate → Ethyl 2,9-diethoxycarbonylnonanoate

HRID 2268440Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2268440
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[O-]CC.[Na+].Br[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25].[Cl-].[NH4+]>C(O)C>[CH2:10]([O:9][C:1]([CH:2]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:3]([O:5][CH2:6][CH3:7])=[O:4])=[O:8])[CH3:11]

Komponenten

6

Edukt 4

HCID 7761Diethyl MalonateHCID 25517Ammonium ChlorideHCID 264813Ethyl 8-bromooctanoateHCID 2723922Sodium ethoxide

Produkt 1

HCID 18348648Ethyl 2,9-diethoxycarbonylnonanoateAusbeute 67,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Diethyl malonate (9.85 g, 61.5 mmols) was added to an ethanol (170 ml) solution of sodium ethoxide (4.61 g, 67.7 mmols) with cooling with ice, and then stirred for 15 minutes at room temperature, and thereafter ethyl 8-bromooctanoate (17.0 g, 67.7 mmols) was added thereto. The reaction mixture was heated under reflux for 2 hours, and then an aqueous saturated ammonium chloride solution was added thereto, and extracted with ethyl acetate. The organic layer was washed with water and a saturated aqueous sodium chloride solution, then dried, and concentrated in vacuo. The thus-obtained crude product was purified by silica gel column chromatography (hexane:ethyl acetate=20:1) to obtain the entitled compound (13.7 g) as an oil.

Aufarbeitung

  1. temperaturewith cooling with ice
  2. temperatureThe reaction mixture was heated
  3. temperatureunder reflux for 2 hours
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materiala saturated aqueous sodium chloride solution, then dried
  7. concentrationconcentrated in vacuo
  8. customThe thus-obtained crude product
  9. customwas purified by silica gel column chromatography (hexane:ethyl acetate=20:1)

Quellen und Nachweise

ORD-Eintrag
ord-33d2b3341d964e5e945fa83036a9038e
Quelldatensatz
uspto-grants-2001_12
Patentnummer
US06326369B1

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