Iodoethane → HCID 58863679, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of diisopropylamine (0.42 g, 4.15 mmol) in tetrahydrofuran (7 ml) was added n-butyl lithium in hexane (1.56M, 2.2 ml, 3.43 mmol) under ice cooling, and the mixture was stirred for 15 minutes at 0° C. Thereto was added dimethyl (3-iodobenzyl)malonate (0.98 g, 2.82 mmol) in tetrahydrofuran (8 ml) under ice cooling, and the mixture was stirred for 10 minutes at 0° C. Thereto was added ethyl iodide (0.70 g, 4.49 mmol) and the mixture was stirred for 1 hour at 60° C. Additional ethyl iodide (0.60 g, 3.85 mmol) was added thereto and the mixture was stirred for 3 hours at 60° C. The reaction was quenched by an aqueous 5% potassium hydrogensulfate solution and extracted with ethyl acetate. The organic layer was washed with an aqueous saturated sodium chloride solution, and dried over magnesium sulfate. The solvent was removed and the residue was purified with silica gel chromatography (hexane:ethyl acetate=4:1→3:1) to give the subject compound (0.78 g, 73%).

Provenance & Evidence