Ethyl Acetate → HCID 69517064, compound

Participants

Reaction Steps

To a solution of (2-trityl-2H-tetrazol-5-yl)-acetonitrile (2.0 g, 5.69 mmol) in 25 mL benzene was added 2-n-propylvaleraldehyde (0.87 g, 6.79 mmol), 25 mL 10% NaOH (aq), and tetrabutylammonium bromide (50 mg). The mixture was stirred for 1 h, then poured into EtOAc. The phases were separated, and the organic phase dried (MgSO4) and concentrated. Flash chromatography of the residue (10→15% EtOAc/hexanes) provided 1.66 g (64%) of 4-propyl-2-(2-trityl-2H-tetrazol-5-yl)-hept-2-enenitrile as a colorless solid. 1H NMR (CDCl3) δ 7.34 (m, 10H, —CHCH═C—), 7.09 (m, 6H), 2.86 (m, 1H, —CH2CH—), 1.30-1.59 (m, 8H, —CH2CH2—), 0.90 (t, J=7.1 Hz, 6H, CH3—).

Provenance & Evidence