1-Methyl-3-(trifluoromethyl)-1H-pyrazole-5-carboxylic acid → (1-Methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)methanol

Participants

Reaction Steps

1-Methyl-3-(trifluoromethyl)-1H-pyrazole-5-carboxylic acid BB4a (837 mg, 4.3 mmol) is dissolved in anhydrous tetrahydrofurane (10 mL), then LiAlH4 (2.16 mL of 2.0 M in tetrahydrofurane, 4.3 mmol) is added dropwise and stirred at rt for 1 h. The mixture is quenched by dropwise addition of 1N HCl, then is made basic by addition of saturated NaHCO3 and extracted with EtOAc (3×). The organic layers are combined, washed with brine, dried (MgSO4), filtered and concentrated to provide (1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)methanol BB4b as a clear oil. 1H NMR (400 MHz, CDCl3) δ=6.46 (s, 1H), 4.69 (d, J=5.6 Hz, 2H), 3.95 (s, 3H); MS calcd. for C6H8F3N2O ([M+H]+): 181.0, found: 181.1.

Provenance & Evidence