Hydrochloric Acid → Ethyl 2-formyl-1,3-thiazole-4-carboxylate

HRID 2203117Notes

Reaction equation

HRID 2203117 reaction equation
C([O:3][CH:4](OCC)[C:5]1[S:6][CH:7]=[C:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[N:9]=1)C.Cl>CC(C)=O>[CH:4]([C:5]1[S:6][CH:7]=[C:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[N:9]=1)=[O:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 16220290Ethyl 2-(diethoxymethyl)thiazole-4-carboxylate

Product 1

HCID 11355896Ethyl 2-formyl-1,3-thiazole-4-carboxylateYield 87.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of ethyl 2-(diethoxymethyl)thiazole-4-carboxylate (1.6 g) and 1 M HCl (12.3 ml) in acetone (100 ml) was heated under reflux for 5 h. After the solvent was removed by evaporation, the residue was diluted with AcOEt, neutralized with saturated NaHCO3 solution and extracted with EtOAc. The organic layer was separated, washed with water and brine successively, dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane/EtOAc) to give the title compound (1.0 g) as an off-white solid.

Workup

  1. temperatureunder reflux for 5 h
  2. customAfter the solvent was removed by evaporation
  3. additionthe residue was diluted with AcOEt
  4. extractionextracted with EtOAc
  5. customThe organic layer was separated
  6. washwashed with water and brine successively
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by silica gel column chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-81bacc2ef6d94b1498acabc9518bb46a
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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