Methyl 2-(1H-pyrrol-1-yl)benzoate → (2-(1H-pyrrol-1-yl)phenyl)methanol

HRID 845381

Reaktionsgleichung

Reaktionsgleichung von HRID 845381
[H-].[Al+3].[Li+].[H-].[H-].[H-].[N:7]1([C:12]2[CH:21]=[CH:20][CH:19]=[CH:18][C:13]=2[C:14](OC)=[O:15])[CH:11]=[CH:10][CH:9]=[CH:8]1>CCOCC>[N:7]1([C:12]2[CH:21]=[CH:20][CH:19]=[CH:18][C:13]=2[CH2:14][OH:15])[CH:11]=[CH:10][CH:9]=[CH:8]1

Komponenten

4

Edukt 2

HCID 2776733Methyl 2-(1H-pyrrol-1-yl)benzoateHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 7016493(2-(1H-pyrrol-1-yl)phenyl)methanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

To a suspension of 117 g of lithium aluminum hydride in 2 L of anhydous ether (under an inert atmosphere) is added dropwise a solution of 428 g of methyl 2-(pyrrol-1-yl)-benzoate in 1.5 L of ether over a period of 4 hours. The reaction mixture is then heated at reflux temperature for an additional 4 hours and then allowed to cool to room temperature. After cooling in an ice-bath, the excess lithium aluminum hydride is destroyed by the dropwise addition of 117 ml of water over 1 hour, followed by dropwise addition of 117 ml of 15% sodium hydroxide and subsequent addition of 351 ml of water over a 30 minute period. The resultant granular solid is separated by filtration, the ether layer is then dried over magnesium sulfate and the solvent evaporated under reduced pressure to yield 2-(pyrrol-1-yl)-benzyl alcohol which may be further purified by distillation in vacuo; b.p. 110°-114°/0.1 mm Hg.

Aufarbeitung

  1. temperatureThe reaction mixture is then heated
  2. temperatureat reflux temperature for an additional 4 hours
  3. temperatureAfter cooling in an ice-bath
  4. customthe excess lithium aluminum hydride is destroyed by the dropwise addition of 117 ml of water over 1 hour
  5. additionfollowed by dropwise addition of 117 ml of 15% sodium hydroxide and subsequent addition of 351 ml of water over a 30 minute period
  6. customThe resultant granular solid is separated by filtration
  7. dry with materialthe ether layer is then dried over magnesium sulfate
  8. customthe solvent evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-908f4a4bfcfa4dfbaac2ca7c4256db44
Quelldatensatz
uspto-grants-1988_07
Patentnummer
US04758559

Verknüpfte Notizen

Wird geladen…