Sodium Iodide → Tert-butyl 1-cyanocyclobutane-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

A solution of tert-butyl 2-cyanoacetate (4.0 g, 28.3 mmol), 1,3-dibromopropane (6.29 g, 31.2 mmol) in methyl ethyl ketone (100 ml) was treated with potassium carbonate (11.75 g, 85 mmol). The reaction mixture was heated to 80° C. for 17 h and then NaI (catalyst) (0.21 g, 1.42 mmol) was added. The mixture was heated at 80° C. for 6 days and then allowed to cool to RT. The mixture was filtered through Celite® (filter material) and the filtrate was concentrated in vacuo. Purification by chromatography on silica eluting with 10% EtOAc in iso-hexane afforded the title product as a colourless oil; 1H NMR (400 MHz, CDCl3) δ 2.64 (4H, m), 2.22 (2H, m), 1.53 (9H, s).

Provenance & Evidence