Potassium Carbonate → 2-(Hydroxymethyl)thiazole-4-carboxylic acid

Participants

Reaction Steps

A solution of 2-{[(2,2-dimethylpropanoyl)oxy]methyl}-1,3-thiazole-4-carboxylic acid (3 g, 12.33 mmol, commercially available) and potassium carbonate (2.326 g, 16.83 mmol) in methanol (100 mL) and water (30 mL) was heated to reflux for 4 hr. The mixture was cooled and concentrated in vacuo to ˜30 ml. It was then acidified with 2 M HCl (50 ml) and concentrated in vacuo. The resulting solid was treated with hot MeOH/EtOAc (2:1), washing well before filtering off the remaining solid. The filtrate was concentrated in vacuo to give a brown solid which was dissolved in MeOH and added to the top of 2×70 g aminopropyl cartridge that had been preconditioned with MeOH. The cartridges were both eluted with MeOH and then with 10% HCl in MeOH. The acidic fractions were combined and the solvent removed in vacuo to give the title compound as a brown oil (550 mg).

Provenance & Evidence