Menthol → 2-(Pyrrol-1-yl)malonic acid ethyl (-)-menthyl ester

HRID 256581

Reaktionsgleichung

Reaktionsgleichung von HRID 256581
[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].[CH:17]1([CH3:27])[CH2:22]C[CH:20]([CH:23](C)[CH3:24])[CH:19](O)[CH2:18]1>CCO.CCO.CCO.CCO.[Ti]>[CH:23]1([CH3:24])[CH2:20][CH2:19][CH:18]([CH:17]([CH3:27])[CH3:22])[CH:9]([O:8][C:6](=[O:7])[CH:5]([N:11]2[CH:12]=[CH:13][CH:14]=[CH:15]2)[C:4]([O:3][CH2:1][CH3:2])=[O:16])[CH2:10]1

Komponenten

4

Edukt 2

HCID 1254MentholHCID 2782128diethyl 2-(1H-pyrrol-1-yl)malonate

Produkt 1

HCID 538719252-(Pyrrol-1-yl)malonic acid ethyl (-)-menthyl esterAusbeute 31,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2724286Titanium(IV)ethoxideKatalysator

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

To a mixture of 2-(pyrrol-1-yl)malonic acid diethyl ester (300.0 g) and (-)-menthol (417.0 g) was added tetraethyl titanate (10.0 g), and the resulting mixture was stirred at 110° C. for 19 hours. After removal of the (-)-menthol under reduced pressure, the residue was chromatographed on silica gel using n-hexane/ethyl acetate (50:1) as the eluent. Fractions containing the title compound were pooled and evaporated under reduced pressure to give the title compound (142.0 g, 31.8%) as a colorless oil.

Aufarbeitung

  1. customAfter removal of the (-)-menthol under reduced pressure
  2. customthe residue was chromatographed on silica gel
  3. additionFractions containing the title compound
  4. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-f14a8b62c6884870a484f598b5c82ebb
Quelldatensatz
uspto-grants-1993_11
Patentnummer
US05258382

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