Dimethylformamide → Ethyl 4-(hydroxymethyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carboxylate

Participants

Reaction Steps

To a stirred solution of ethyl 4-(bromomethyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carboxylate (50 g, 0.127 moles, 1 eq) in dry DMF (300 ml) under a positive N2 flow was added silver trifluoroacetate (42.02 g, 0.191 moles, 1.5 eq) all at once as a solid. This was stirred at room temperature for 3.5 hrs. The reaction was partitioned between ethyl ether (1.5 L) and water (500 ml). The phases were separated and the organic phase was washed twice with water (500 ml). After separation of the phases, the organic fraction was dried with Na2SO4, filtered and concentrated in vacuo. The crude trifluoroacetate product was used without characterization. Ethanol (300 ml) was added and the reaction was refluxed for 10 hrs. After cooling to room temperature the ethanol was removed in vacuo to yield 42 g (100%) of the title compound. The product was used without purification.

Provenance & Evidence