Borane;tetrahydrofuran → 2-(5-Methyl-2-(4-(trifluoromethyl)phenyl)oxazol-4-yl)ethanol

Participants

Reaction Steps

7.33 g of the above prepared [5-methyl-2-(4-trifluoromethyl-phenyl)-oxazol-4-yl]-acetic acid (25.7 mmol) was dissolved in 120 ml of abs. THF and treated at 0° C. with 64 ml 1M BH3THF (2.5 eq.). The reaction mixture was then kept over night et ambient temperature. Careful quenching with MeOH and ice, twofold extraction with AcOEt, washing with water and brine, drying over magnesium sulfate, and evaporation of the solvents left a crude product which was refluxed for 30 min. in MeOH to liberate quantitatively the free alcohol. Flash chromatography (SiO2, hexane/AcOEt=7/3) delivered finally 6.38 g of the title compound as off-white crystals.

Provenance & Evidence