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

HRID 1881883Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1881883
[O:1]1CCO[CH:2]1[C:6]1[S:7][C:8]([C:11]([OH:18])([CH3:17])[CH:12]([O:15][CH3:16])[O:13][CH3:14])=[CH:9][N:10]=1.Cl.C(=O)([O-])O.[Na+]>CC(C)=O>[OH:18][C:11]([C:8]1[S:7][C:6]([CH:2]=[O:1])=[N:10][CH:9]=1)([CH3:17])[CH:12]([O:13][CH3:14])[O:15][CH3:16]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 593316132-[2-(1,3-Dioxolan-2-yl)-1,3-thiazol-5-yl]-1,1-dimethoxypropan-2-ol

Produkt 1

HCID 593315475-(1-Hydroxy-2,2-dimethoxy-1-methylethyl)-1,3-thiazole-2-carbaldehydeAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of 2-[2-(1,3-dioxolan-2-yl)-1,3-thiazol-5-yl]-1,1-dimethoxypropan-2-ol (1.58 g), 1M hydrochloric acid (5 ml) and acetone (15 mL) was stirred overnight at 60° C. 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 (0.94 g, yield 71%) was obtained as colorless crystals from a fraction eluted with ethyl acetate-hexane (4:1, volume ratio). melting point 98-99° C.

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-692c64a81e4545a890496d866fd52804
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08318746B2

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