Hydrochloric Acid → 5-[(2-Methoxyethoxy)methyl]-1,3-thiazole-2-carbaldehyde

HRID 1881880Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1881880
[O:1]1CCO[CH:2]1[C:6]1[S:7][C:8]([CH2:11][O:12][CH2:13][CH2:14][O:15][CH3:16])=[CH:9][N:10]=1.Cl.C(=O)([O-])O.[Na+]>CC(C)=O>[CH3:16][O:15][CH2:14][CH2:13][O:12][CH2:11][C:8]1[S:7][C:6]([CH:2]=[O:1])=[N:10][CH:9]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 593316232-(1,3-Dioxolan-2-yl)-5-[(2-methoxyethoxy)methyl]-1,3-thiazole

Produkt 1

HCID 593313455-[(2-Methoxyethoxy)methyl]-1,3-thiazole-2-carbaldehydeAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A mixture of 2-(1,3-dioxolan-2-yl)-5-[(2-methoxyethoxy)methyl]-1,3-thiazole (0.40 g), 1M hydrochloric acid (2 mL) and acetone (10 mL) was stirred with heating under reflux for 4 hr. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate, 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 (0.26 g, yield 81%) was obtained as a colorless oil from a fraction eluted with ethyl acetate-hexane (3:1, volume ratio).

Aufarbeitung

  1. temperaturewith heating
  2. temperatureunder reflux for 4 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with saturated brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-98719fe730c84549a0accb5768b49e35
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08318746B2

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