Ethyl 2-(diethoxymethyl)thiazole-4-carboxylate → Ethyl 2-formyl-1,3-thiazole-4-carboxylate

HRID 244652Notes

Reaction equation

HRID 244652 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 1

HCID 16220290Ethyl 2-(diethoxymethyl)thiazole-4-carboxylate

Product 1

HCID 11355896Ethyl 2-formyl-1,3-thiazole-4-carboxylateYield 97.6%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 313Hydrochloric AcidSolvent

Procedure

A solution of ethyl 2-[bis(ethyloxy)methyl]-1,3-thiazole-4-carboxylate (455 mg) in 10% 1M hydrochloric acid in acetone (50 ml) was heated at reflux for 1 h. The mixture was concentrated in vacuo, taken up in DCM (20 ml) and washed with saturated sodium bicarbonate solution (10 ml). The organic layer was separated using a hydrophobic frit and evaporated to give the title compound (317 mg) as a yellow solid.

Workup

  1. temperatureat reflux for 1 h
  2. concentrationThe mixture was concentrated in vacuo
  3. washwashed with saturated sodium bicarbonate solution (10 ml)
  4. customThe organic layer was separated
  5. customevaporated

Sources & evidence

ORD record
ord-8b26753199ef4372a0c393a59c494455
Source dataset
uspto-grants-2014_02
Patent number
US08658635B2

Reaction notes

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