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

HRID 1677769Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1677769
[OH:1][C@H:2]([C@H:6]([CH3:10])[C:7]([OH:9])=[O:8])[C:3]([OH:5])=[O:4].CO[C:13](OC)([CH3:15])[CH3:14]>CC(C)=O.[Cu](Cl)Cl>[CH3:14][C:13]1([CH3:15])[O:1][C@H:2]([C@H:6]([CH3:10])[C:7]([OH:9])=[O:8])[C:3](=[O:5])[O:4]1

Komponenten

5

Edukt 2

HCID 64952,2-DimethoxypropaneHCID 440892D-Erythro-3-Methylmalate

Produkt 1

HCID 58488020(2S)-2-[(4R)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]propanoic acidAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24014Cupric ChlorideKatalysatorHCID 180AcetoneLösungsmittel

Versuchsvorschrift

To a solution of (2R,3S)-2-hydroxy-3-methylsuccinic acid (2.48 g; 16.8 mmol; 1.0 eq.) in acetone (80.0 mL) was added 2,2-dimethoxypropane (4.13 g; 33.6 mmol; 2.0 eq.) and copper(II) chloride (226 mg; 1.68 mmol; 0.1 eq.). The resulting reaction mixture was stirred for 16 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 (mixture of diastereoisomers) as a greenish oil (1.85 g, 59%) 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-3b476f077ca3428db38b285de435ca73
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08008302B2

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