1,3-Diethyl 2-(4-aminophenyl)propanedioate → 2-(4-Aminophenyl)propane-1,3-diol

HRID 28621Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 28621
C([O:3][C:4](=O)[CH:5]([C:11]1[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=1)[C:6](OCC)=[O:7])C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>CCOCC>[NH2:17][C:14]1[CH:13]=[CH:12][C:11]([CH:5]([CH2:6][OH:7])[CH2:4][OH:3])=[CH:16][CH:15]=1

Komponenten

4

Edukt 2

HCID 124708371,3-Diethyl 2-(4-aminophenyl)propanedioateHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 195939762-(4-Aminophenyl)propane-1,3-diolAusbeute 17,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To a solution of 2-(4-amino-phenyl)-malonic acid diethyl ester (450 mg, 1.8 mmol) in anhydrous ether (20 ml), cooled at 0-10° C., was added lithium aluminum hydride (68 mg, 1.8 mmol). After stirring at room temperature for 2 hours, the reaction was cooled to 10° C. and quenched by the addition of hydrated sodium sulfate (2 g). The mixture was filtered and the solid was rinsed with tetrahydrofuran (10 ml). The combined filtrates were concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with 20% methanol-chloroform to provide 2-(4-amino-phenyl)-propane-1,3-diol (52 mg, 17% yield).

Aufarbeitung

  1. temperaturethe reaction was cooled to 10° C.
  2. customquenched by the addition of hydrated sodium sulfate (2 g)
  3. filtrationThe mixture was filtered
  4. washthe solid was rinsed with tetrahydrofuran (10 ml)
  5. concentrationThe combined filtrates were concentrated under reduced pressure
  6. customThe residue was purified by flash chromatography on silica gel eluting with 20% methanol-chloroform

Quellen und Nachweise

ORD-Eintrag
ord-3a5f2e55380a46d2918588bd06ad3564
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07419984B2

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