Sodium Chloride → HCID 14999092, compound

Participants

Reaction Steps

Dry diisopropylamine (2.76 ml, 15.8 mmol) was added to dry tetrahydrofuran (9 ml). Further a n-butyllithium solution (10.6 ml, 16.2 mmol) in hexane was added dropwise at -20° to -30° C. The mixture was kept between those temperatures for 1 hour. Then a solution of 3-methyl-2-(3-pyridyl)thiazolidin-4-one (3 g, 15.4 mmol) in dry tetrahydrofuran was added dropwise at -78° C. After this reaction mixture had been kept at the same temperature for 1 hour, bromomethylcyclohexane (3.01 g, 17.0 mmol) and sodium iodide (2.31 g, 15.4 mmol) were added at -78° C. This reaction mixture was heated up to room temperature and kept standing overnight. The resulting mixture, after addition of aqueous NaCl, was extracted with ethyl acetate. The extract was washed with aqueous NaCl, dried, and the solvent was removed in vitro. The residue was chromatographed on silica gel, giving 5,5-di(cyclohexylmethyl)-3-methyl-2-(3-pyridyl)thiazolidin-4-one (250 mg, 4.2% yield). IR (CHCl3) [cm-1 ]; 2920, 1675, 1640, 1390.

Provenance & Evidence