Hydrochloric Acid → 2-Thiazolecarboxaldehyde, 5-(2,2,2-trifluoro-1-hydroxyethyl)-

HRID 1881886Notes

Reaction equation

HRID 1881886 reaction equation
[O:1]1CCO[CH:2]1[C:6]1[S:7][C:8]([CH:11]([OH:16])[C:12]([F:15])([F:14])[F:13])=[CH:9][N:10]=1.Cl.O1CCCC1>O>[F:14][C:12]([F:13])([F:15])[CH:11]([C:8]1[S:7][C:6]([CH:2]=[O:1])=[N:10][CH:9]=1)[OH:16]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 593313011-[2-(1,3-Dioxolan-2-yl)-1,3-thiazol-5-yl]-2,2,2-trifluoroethanol

Product 1

HCID 593313142-Thiazolecarboxaldehyde, 5-(2,2,2-trifluoro-1-hydroxyethyl)-Yield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1-[2-(1,3-dioxolan-2-yl)-1,3-thiazol-5-yl]-2,2,2-trifluoroethanol (2.56 g), 1M hydrochloric acid (10 mL) and tetrahydrofuran (10 mL) was stirred with heating under reflux for 6 hr. Water was added to the reaction mixture, 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 (1.69 g, yield 80%) was obtained as colorless crystals from a fraction eluted with ethyl acetate-hexane (4:1, volume ratio). melting point 64-66° C.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 6 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-86427174221c443b97314867fd375ab7
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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