Benzyl Alcohol → HCID 54532374, Verbindung

HRID 256580

Reaktionsgleichung

Reaktionsgleichung von HRID 256580
[CH2:1]([O:3][C:4](=[O:16])[CH:5]([N:11]1[CH:15]=[CH:14][CH:13]=[CH:12]1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].C(O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20]C=1>CCO.CCO.CCO.CCO.[Ti]>[CH2:9]([O:8][C:6](=[O:7])[CH:5]([N:11]1[CH:12]=[CH:13][CH:14]=[CH:15]1)[C:4]([O:3][CH2:1][C:2]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:18]=1)=[O:16])[C:10]1[CH:18]=[CH:23][CH:22]=[CH:21][CH:20]=1

Komponenten

4

Edukt 2

HCID 244Benzyl AlcoholHCID 2782128diethyl 2-(1H-pyrrol-1-yl)malonate

Produkt 1

HCID 54532374HCID 54532374, VerbindungAusbeute 87,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2724286Titanium(IV)ethoxideKatalysator

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

To a solution of 2-(pyrrol-1-yl)malonic acid diethyl ester (75.7 g) in benzyl alcohol (200 ml) was added tetraethyl titanate (3.0 g), and the resulting mixture was stirred at 110° C. for 15 hours. After removal of the benzyl alcohol under reduced pressure, the residue was chromatographed on silica gel using n-hexane/ethyl acetate (10:1) as the eluent. Fractions containing the title compound were pooled and evaporated under reduced pressure. The residue was recrystallized from ethyl acetate/n-hexane to give the title compound (102.5 g, 87.3%) as colorless crystals, mp 48.5°-49° C.

Aufarbeitung

  1. customAfter removal of the benzyl alcohol under reduced pressure
  2. customthe residue was chromatographed on silica gel
  3. additionFractions containing the title compound
  4. customevaporated under reduced pressure
  5. customThe residue was recrystallized from ethyl acetate/n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-32045007fac441dfb7bc1bce30e13674
Quelldatensatz
uspto-grants-1993_11
Patentnummer
US05258382

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