Hexane → Ethyl 5-phenylpent-2-enoate

Participants

Reaction Conditions

Reaction Steps

The reagents DCC (33 mM) and DMAP (30 mM) were added to a solution of 5-phenylpent-2-enoic acid (5.3 g, 30 mM) in EtOH (50 mL) and THF (20 mL), which was cooled to 0° C. The resulting mixture was stirred for 30 min at 0° C., then allowed to react for 15 h at room temperature. The suspension was filtered, and the filtrate was concentrated. The residue was dissolved in EtOAc and washed with 1 M HCl (3×30 mL), H2O (10 mL), saturated NaHCO3 (3×30 mL), H2O (10 mL), saturated NaCl (20 mL), dried over MgSO4, and concentrated. Chromatography on a silica gel column using 1:2 EtOAc:hexane as the eluent afforded 5-phenyl-pent-2-enoic acid ethyl ester (3.75 g, yield=61%).

Provenance & Evidence