Citric Acid → 1-[2-(1,3-Dioxolan-2-yl)-1,3-thiazol-5-yl]ethanol

HRID 1881871Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1881871
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[S:7][C:8]([CH:11]=[O:12])=[CH:9][N:10]=1.[C:13](O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1>[O:3]1[CH2:4][CH2:5][O:1][CH:2]1[C:6]1[S:7][C:8]([CH:11]([OH:12])[CH3:13])=[CH:9][N:10]=1

Komponenten

4

Edukt 2

HCID 311Citric AcidHCID 593313182-(1,3-Dioxolan-2-yl)-1,3-thiazole-5-carbaldehyde

Produkt 1

HCID 593314621-[2-(1,3-Dioxolan-2-yl)-1,3-thiazol-5-yl]ethanolAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 2-(1,3-dioxolan-2-yl)-1,3-thiazole-5-carbaldehyde (2.25 g) in tetrahydrofuran (20 mL) was slowly added a 1.13M methyllithium diethyl ether solution (12.0 mL) at 0° C. under a nitrogen atmosphere. The reaction mixture was stirred at 0° C. for 30 min, 10% aqueous citric acid solution was added, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The obtained residue was subjected to silica gel column chromatography, and the title compound (1.96 g, yield 80%) was obtained as a colorless oil from a fraction eluted with ethyl acetate-hexane (1:2, volume ratio). MS: 202 (MH+).

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-e1a5fa507f894b018c62435913b5fc4d
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08318746B2

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