Potassium Hydroxide → 4-(3-Cyclopentylpropyl)-1-Phenyl-5-Tetrazolone

Participants

Reaction Conditions

Reaction Steps

To a solution of 600 mg of 1-phenyl-5-tetrazolone (for the synthesis of this compound see: Horwitz, J. P.; Fisher, B. E.; Tomasewski, A. J. J Amer Chem Soc 1959, 81, 3076) in 2 mL of N,N-dimethylformamide (DMF) was added 280 mg of powdered 85% potassium hydroxide followed by 870 mg of 3-cyclopentyl-1-iodopropane from Step A. The mixture was stirred at 80° C. for 18 h and then quenched by addition of water. The product was extracted with dichloromethane and purification by flash chromatography on silica gel (9:1 hexane:ethyl acetate) afforded 830 mg of the title compound: 1H NMR (CDCl3) δ7.96 (d, 2H, J=8.5 Hz), 7.50 (t, 2H, J=7.5 Hz), 7.37 (t, 1H, J=7.5 Hz), 4.02 (t, 2H, J=7.1 Hz), 1.90 (m, 3H), 1.79 (m, 2H), 1.61 (m, 2H), 1.53 (m, 2H), 1.41 (m, 2H), 1.10 (m, 2H).

Provenance & Evidence