(+-)-3-Phenyllactic acid → HCID 4292412, Verbindung

HRID 732859Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 732859
[CH:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH:8]([OH:12])[C:9]([OH:11])=[O:10])=[CH:3][CH:2]=1.C([O-])([O-])=O.[Cs+].[Cs+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C=O)C.CCOC(C)=O>[CH2:19]([O:10][C:9](=[O:11])[CH:8]([OH:12])[CH2:7][C:4]1[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Komponenten

6

Edukt 3

HCID 3848(+-)-3-Phenyllactic acidHCID 7498Benzyl BromideHCID 10796Cesium carbonate

Produkt 1

HCID 4292412HCID 4292412, VerbindungAusbeute 93,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of DL-Phenyllactic acid (5.0 g, 30.09 mmol) in DMF (30 mL) was added Cs2CO3 (10.79 g, 33.11 mmol) in portions during 10 minutes period at room temperature. The resulting mixture was stirred for 15 min at room temperature, followed by the addition of benzyl bromide (3.57 mL, 30.09 mmol). The resulting mixture was stirred at room temperature overnight. The reaction mixture was diluted with EtOAc (300 mL), washed with saturated NaHCO3, water (100×2) and brine, dried (Na2SO4) and filtered. The filtrate was concentrated to give 7.20 g (89%) of the title compound.

Aufarbeitung

  1. stirringThe resulting mixture was stirred at room temperature overnight
  2. washwashed with saturated NaHCO3, water (100×2) and brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-c90f5ecad0e44e6b8f16ab6123e32b3c
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07589067B2

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