Cyclopentanone → HCID 69516114, compound

Participants

Reaction Conditions

Reaction Steps

To a flask charged with dry sodium hydride (0.32 g, 13.3 mmol) was added (2-trityl-2H-tetrazol-5-yl)-acetonitrile (2.34 g, 6.67 mmol). The solids were swirled to mix, cooled to 0° C., and 25 mL THF was added quickly, resulting in vigorous H2 evolution and a bright yellow foam. The mixture was stirred at 0° C. for 5 min, at which time the ice bath was removed and stirring continued for 10 min. Cyclopentanone (0.65 mL, 7.33 mmol) in 10 mL THF was added quickly resulting in a clear orange solution. The mixture was stirred for 2 h, partitioned between EtOAc and sat. NH4Cl (aq), and the organic phase dried (MgSO4) and concentrated. Flash chromatography of the residue (CH2Cl2) furnished 2.05 g (74%) of cyclopentylidene-(2-trityl-2H-tetrazol-5-yl)-acetonitrile as a white solid. 1H NMR (CDCl3) δ 7.32 (m, 9H), 7.10 (m, 6H), 2.86 (m, 4H, —CH2CCH2—), 1.84 (m, 4H, —CH2CH2CH2CH2—).

Provenance & Evidence