Hexane → HCID 10220629, compound

Participants

Reaction Steps

A stirred slurry of hexane washed potassium hydride (0.87 g, 21.8 mmol) in 50 mL of dry THF was treated portionwise with 5-chloroindole (3.3 g, 21.8 mmol). The mixture was heated at reflux until a clear solution was obtained. A solution of isopropyl isothiocyanate (2.2 g, 21.8 mmol) in 5 mL THF was slowly added and stirring was continued for 1 hour. The solvent was evaporated and the residue partitioned between EtOAc and 1N HCl. The organic layer was washed with brine, dried over Na2SO4 and concentrated in vacuo. The amber solids were recrystallized from EtOH to provide 3.4 g of the title compound as a tan solid, m.p. 135° C. (62% of theory).

Provenance & Evidence