Tetrahydrofuran → 2,2-Diethyl-1,2-dihydroquinoline

Participants

Reaction Steps

This compound was prepared in a manner similar to that described for 1,2-Dihydro-2,2-dimethylquinoline (structure 17 of Scheme III, where R1=R2=Me) from 2-ethyl-1-pentyn-3-yl(phenyl)amine (3.00 g, 16.0 mmol) and CuCl (0.190 g, 1.92 mmol) in THF to afford 1.51 g (50%) of 2,2-diethyl-1,2-dihydroquinoline after flash chromatography (hexanes:EtOAc, 16:1). Data for 2,2-diethyl-1,2-dihydroquinoline: Rf 0.44 (16:1 hexanes:EtOAc; 1H NMR (400 MHz, CDCl3) 6.85-6.95 (m, 1H), 6.81 (d, J=7.3, 1H), 6.48 (t, J=7.3, 1H), 6.36 (d, J=9.9, 1H), 5.21 (d, J=9.9, 1H), 3.39 (broad s, 1H), 1.35-1.55 (m, 4H), 0.93 (t, J=7.5, 6H).

Provenance & Evidence