4-Methyl-2-(4-(trifluoromethyl)phenyl)-5-thiazolecarboxylic acid → (4-Methyl-2-(4-(trifluoromethyl)phenyl)-1,3-thiazol-5-yl)methanol

Participants

Reaction Conditions

Reaction Steps

Cool (0° C.) a solution of lithium aluminum hydride (10 mL, 1M in THF) and add a solution of 4-methyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid (Commercially available, 2.87 g, 10 mmol) in THF (20 mL). On complete addition, remove the cold bath and stir for 3.5 hrs. Cool this solution to 5° C., and then add water (0.25 mL), dropwise, followed by NaOH solution (0.25 mL, 5M in water) and water (0.5 mL). Dilute the resulting mixture with ethyl acetate and then filter through a pad of celite. Wash the solids with dichloromethane and then concentrate the combined filtrates under reduced pressure to give the title compound as a yellow solid (2.59 g).

Provenance & Evidence