HCID 11652360, compound → (4-Methyl-2-(4-(trifluoromethyl)phenyl)-1,3-thiazol-5-yl)methanol

Participants

Reaction Conditions

Reaction Steps

Methyl 4-methyl-2-[4-(trifluoromethyl)phenyl]]thiazole-5-carboxylate (20.0 g, 66.4 mmol) obtained from Example 1 was dissolved in anhydrous dichloromethane (500 ml) under nitrogen atmosphere, and the reaction mixture was cooled to −78° C. Diisobutyl aluminum hydride (DIBAL-H, 166 ml, 1.0 M hexane solution, 2.5 eq.) was slowly added to the solution for 30 minutes, and the mixture was reacted for another 30 minutes at the same temperature. Subsequently, the temperature was raised to −10° C. and reacted for 30 minutes. After completion of the reaction, an excessive diisobutyl aluminum hydride was removed by ethyl acetate. The resultant residue was extracted by 10% sulfuric acid and ethyl acetate, followed by drying over magnesium sulfate. The resultant mixture was purified on silica flash column, followed by evaporation under reduced pressure to thereby yield 17.5 g of the title compound (yield: 96.4%).

Provenance & Evidence