2,2-Dimethoxypropane → (2R)-2-[(4S)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]-3-phenylpropanoic acid

HRID 1677772Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1677772
[CH2:1]([C@H:8]([C@H:12]([OH:16])[C:13]([OH:15])=[O:14])[C:9]([OH:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO[C:19](OC)([CH3:21])[CH3:20]>CC(C)=O.[Cu](Cl)Cl>[CH3:20][C:19]1([CH3:21])[O:16][C@@H:12]([C@@H:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:9]([OH:11])=[O:10])[C:13](=[O:15])[O:14]1

Komponenten

5

Edukt 2

HCID 64952,2-DimethoxypropaneHCID 54300227(2R,3S)-2-benzyl-3-hydroxysuccinic acid

Produkt 1

HCID 58488000(2R)-2-[(4S)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]-3-phenylpropanoic acidAusbeute 72,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24014Cupric ChlorideKatalysatorHCID 180AcetoneLösungsmittel

Versuchsvorschrift

To a solution of (2R,3S)-2-benzyl-3-hydroxysuccinic acid (1.70 g; 7.58 mmol; 1.0 eq.) in acetone (50.0 mL) was added 2,2-dimethoxypropane (1.86 g; 15.2 mmol; 2.0 eq.) and copper(II) chloride (102 mg; 0.76 mmol; 0.1 eq.). The resulting reaction mixture was stirred for 2 h at RT. The reaction mixture was evaporated and the residue taken up in CHCl3. Activated charcoal is added and the resulting mixture stirred for one hour. Filtration on a pad of celite gave the title product as a greenish oil (1.46 g) used in the next step without further purification.

Aufarbeitung

  1. customThe resulting reaction mixture
  2. customThe reaction mixture was evaporated
  3. additionActivated charcoal is added
  4. stirringthe resulting mixture stirred for one hour
  5. filtrationFiltration on a pad of celite

Quellen und Nachweise

ORD-Eintrag
ord-4faa6f8768e34a7f9d7396562b7d6d42
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08008302B2

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