Aluminium lithium hydride → [2-Pyridazin-4-yl-4-(trifluoromethyl)phenyl]methanol

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 2-pyridazin-4-yl-4-(trifluoromethyl)benzoate (Preparation 31, 510 mg, 1.72 mmol) in tetrahydrofuran (15 mL) cooled to 0° C. was added lithium aluminium hydride (2.0 M in tetrahydrofuran, 0.86 mL, 1.72 mmol) dropwise. The reaction was stirred for 1 hour at 0° C. before warming to room temperature and stirring for a further 2 hours. The reaction was re-cooled to 0° C. before excess lithium aluminium hydride was quenched by the addition of water (65 μL), 2M aqueous solution of sodium hydroxide (130 μL) and further water (195 μL). Diethyl ether and anhydrous magnesium sulphate were added to aid the formation of a granular solid which was filtered. The organics were concentrated in vacuo and re-dissolved in dichloromethane (5 mL). The organics were purified by silica gel column chromatography (ISCO™ companion, 40 g column, eluting with 100% heptane to 100% ethyl acetate to 5% methanol in ethyl acetate). Fractions containing product were combined and concentrated in vacuo to obtain the title compound as a yellow solid (197 mg, 45%).

Provenance & Evidence