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

HRID 1881872Notes

Reaction equation

HRID 1881872 reaction equation
[O:1]1CCO[CH:2]1[C:6]1[S:7][C:8]([CH:11]([OH:13])[CH3:12])=[CH:9][N:10]=1.Cl.C(=O)([O-])O.[Na+]>CC(C)=O>[OH:13][CH:11]([C:8]1[S:7][C:6]([CH:2]=[O:1])=[N:10][CH:9]=1)[CH3:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 593314621-[2-(1,3-Dioxolan-2-yl)-1,3-thiazol-5-yl]ethanol

Product 1

HCID 593313835-(1-Hydroxyethyl)-1,3-thiazole-2-carbaldehydeYield 39.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 1-[2-(1,3-dioxolan-2-yl)-1,3-thiazol-5-yl]ethanol (1.96 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 (0.60 g, yield 39%) was obtained as a colorless oil from a fraction eluted with ethyl acetate-hexane (2:1, volume ratio). MS: 158 (MH+).

Workup

  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

Sources & evidence

ORD record
ord-9469dd9105bd49e7a5be4460d109cbb3
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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