Hydrochloric Acid → 5-(1-Hydroxy-2-methoxyethyl)-1,3-thiazole-2-carbaldehyde

HRID 1881876Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1881876
[O:1]1CCO[CH:2]1[C:6]1[S:7][C:8]([CH:11]([OH:15])[CH2:12][O:13][CH3:14])=[CH:9][N:10]=1.Cl.C(=O)([O-])O.[Na+]>CC(C)=O>[OH:15][CH:11]([C:8]1[S:7][C:6]([CH:2]=[O:1])=[N:10][CH:9]=1)[CH2:12][O:13][CH3:14]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 593313571-[2-(1,3-Dioxolan-2-yl)-1,3-thiazol-5-yl]-2-methoxyethanol

Produkt 1

HCID 593316105-(1-Hydroxy-2-methoxyethyl)-1,3-thiazole-2-carbaldehydeAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A mixture of 1-[2-(1,3-dioxolan-2-yl)-1,3-thiazol-5-yl]-2-methoxyethanol (1.84 g), 1M hydrochloric acid (8 mL) and acetone (20 mL) was stirred with heating under reflux for 3 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 (1.04 g, yield 70%) was obtained as a colorless oil from a fraction eluted with ethyl acetate-hexane (2:1, volume ratio). MS: 188 (MH+).

Aufarbeitung

  1. temperaturewith heating
  2. temperatureunder reflux for 3 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-8cb0968a09dc4e479322171a21bd9aec
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08318746B2

Notizen zur Reaktion

Wird geladen…