Chloroform → HCID 18373589, compound

Participants

Reaction Steps

A suspension of NH4Cl (1.38 g, 26 mmol) in dry toluene (8 mL) at 0° C. was treated dropwise with 2-M trimethylaluminium in toluene (13 mL, 26 mmol), allowed to warm to room temperature and stirred for 2 h. This solution was added to a solution of 2-(1-adamantyl)butanenitrile (0.44 g, 2.2 mmol) in dry toluene (10 mL) and the resulting solution refluxed for 4 days, cooled to room temperature and poured into a slurry of SiO2 (5 g) and CHCl3 (10 mL). The slurry was filtered, the filtrate treated with Na2SO4, concentrated in vacuo and the residue loaded on to the top of a silica column and purified by chromatography [SiO2; EtOAc-MeOH (9:1 to 4:1)] to give the title compound (0.38 g, 68%) as a white solid: mp 223° C. (dec); IR νmax (Nujol)/cm−1 3332, 3157, 3071, 2925, 2852, 1666, 1510, 1462, 1377 and 724; NMR δH (400 MHz, DMSO-d6) 0.81 (3H, t, J 7.2 Hz), 1.39 (2H, m), 1.56-1.69 (11H, br m), 1.96 (3H, m), 2.13 (1H, m) and 9.08 (4H, br m); NMR δC (100 MHz, DMSO-d6) 11.8, 17.0, 27.8, 34.1, 36.2, 39.5, 56.0 and 171.0.

Provenance & Evidence