Diethyl Ether → HCID 22609695, compound

Participants

Reaction Conditions

Reaction Steps

A flame dried flask under argon was charged with 2-(4-methylphenyl)adamantane-2-carbonitrile (5.90 g, 23.5 mmol) and anhydrous ether (120 mL) and the solution was cooled to 0° C. Diisobutylaluminium hydride (47 mL, 46.9 mmol, 1-M in heptane) was added dropwise and the reaction left to warm to room temperature. After stirring for 1 h the reaction mixture was quenched with dilute HCl (20 mL) and then filtered through celite. The filtrate was partitioned between EtOAc (100 mL) and water (100 mL), separated, dried (MgSO4) and concentrated in vacuo to afford the title compound (5.11 g, 86%) as a white solid: mp 93-97° C.: NMR δH(400 MHz, CDCl3) 1.61-1.64 (2H, d, J 12.8 Hz), 1.71 (2H, br s), 1.78-1.97 (8H, m), 2.33 (3H, s), 2.86 (2H, br s), 7.18-7.20 (2H, d, J 8.4 Hz), 7.25-7.27 (2H, dd, J 2, 8.4 Hz) and 9.27 (1H, s); Retention time 7.99 min (λ=220 nm).

Provenance & Evidence