Methyl iodide → HCID 14960635, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of naphth-2-ylpropionitrile (25 mmol, 4.52 g) in dry tetrahydrofuran (250 ml) at -78° C. was added n-butyl lithium (30 mmol, 18.75 ml; 1.6M solution in hexane) dropwise over a twenty minute period. After stirring the solution for twenty minutes at -78° C. methyl iodide (30 mmol, 4.26 g) was added in one portion. The reaction mixture was stirred for twenty minutes at -78° C. and the reaction was quenched with saturated NH4Cl (35 ml). The reaction mixture was warmed to room temperature, the volatiles were removed in vacuo, the residue diluted with water (200 ml) and extracted with diethyl ether (2×250 ml). The organic phase was washed with water (250 ml), dried over MgSO4 and concentrated in vacuo. The crude product was purified by preparative high pressure liquid chromatography (SiO2 :hexane/dichloromethane) to give α-methyl-naphth-2-ylpropionitrile as a white solid (3.21 g, 66 percent of theory).

Provenance & Evidence