Aluminium lithium hydride → HCID 58495517, compound

Participants

Reaction Steps

Cool a stirred solution of (E)-5-(2-cyclohexylvinyl)-pyridine-2-carbonitrile (1.76 g, 8.3 mmol) in THF (55 mL) to 0° C. under nitrogen. Carefully add lithium aluminum hydride (1.26 g, 33.2 mmol) and warm to room temperature overnight. Quench the reaction mixture with sequential addition of water (1.26 mL), 15% aqueous NaOH (1.26 mL) and water (3×1.26 mL), and stir for 3 h. Filter the mixture through Celite®, wash with EtOAc, and concentrate in vacuo. Purify the crude mixture by chromatography on silica gel (120 g, pre-packed cartridge) eluting stepwise with DCM/(chloroform:methanol:concentrated NH4OH 80:18:2) (1:0 over 5 min, 49:1 over 5 min, 19:1 over 5 min, 93:7 over 5 min and 9:1 over 5 min; 50 mL/min) to obtain the title compound (608 mg, 34%). MS (APCI+) m/z: 217 (M+H)+.

Provenance & Evidence