Aluminium lithium hydride → HCID 90460626, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred mixture of LiAlH4 (136 mg, 3.58 mmol, 3.99 equiv) in anhydrous tetrahydrofuran (20 mL) maintained under nitrogen at −40° C. was added dropwise a solution of (R/S) ethyl 5-(3-(2-methoxyethoxy)-5-(trifluoromethyl)phenyl)-3-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole-4-carboxylate (410 mg, 0.90 mmol, 1.00 equiv) in tetrahydrofuran (10 mL). The reaction mixture was stirred at −40° C. for 1 h and then quenched with saturated NH4Cl solution (0.2 mL). The solid material was removed by filtration and the filtrate was concentrated under vacuum. The residue was purified on a silica gel column eluted with 30-100% of ethyl acetate in petroleum ether to give 320 mg (86%) of (R/S) (5-(3-(2-methoxyethoxy)-5-(trifluoromethyl)phenyl)-3-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)methanol as a colorless oil. LCMS (method D, ESI): RT=1.51 min, m/z=415.0 [M+H]+.

Provenance & Evidence