2-Indanone → HCID 58107514, Verbindung

HRID 1515477Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1515477
CO[C:3](=O)[CH2:4][CH2:5][NH:6][CH2:7][CH3:8].[CH2:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][C:11]1=[O:19]>C1(C)C=CC=CC=1>[CH2:7]([N:6]1[C:11](=[O:19])[CH2:10][CH2:18][C:17]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=3[CH2:4][C:5]1=2)[CH3:8]

Komponenten

4

Edukt 2

HCID 119832-IndanoneHCID 76973Methyl N-ethyl-beta-alaninate

Produkt 1

HCID 58107514HCID 58107514, VerbindungAusbeute 27,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

3-Ethylamino-propionic acid methyl ester (2.41 g, 18.4 mmol) is added to a solution of 2-indanone (2.3 g, 17.33 mmol) in toluene (27 mL), and the reaction is brought to reflux for 2 hours. Toluene is removed in vacuo and the residue is dissolved in ethylene glycol (23 mL) and the resulting solution is heated to reflux for 8 hours. The reaction is allowed to cool to ambient temperature and is poured over water and extracted with dichloromethane. The organic phase is dried over magnesium sulfate and concentrated in vacuo to afford the crude title compound. The crude product is purified by silica gel chromatography (gradient of ethyl acetate in hexanes 10-100%) affording 1 g (27% yield) of the title compound. MS (m/z): 213.3 (M+1).

Aufarbeitung

  1. temperatureto reflux for 2 hours
  2. customToluene is removed in vacuo
  3. dissolutionthe residue is dissolved in ethylene glycol (23 mL)
  4. temperaturethe resulting solution is heated
  5. temperatureto reflux for 8 hours
  6. additionis poured over water
  7. extractionextracted with dichloromethane
  8. dry with materialThe organic phase is dried over magnesium sulfate
  9. concentrationconcentrated in vacuo
  10. customto afford the crude title compound
  11. customThe crude product is purified by silica gel chromatography (gradient of ethyl acetate in hexanes 10-100%)

Quellen und Nachweise

ORD-Eintrag
ord-26e8f8464bfb47cea31d97303e467b84
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08222424B2

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