Water → 4-Methoxybenzoic acid, 6-aminohexyl ester

Participants

Reaction Steps

A mixture of 4-methoxybenzoic acid, 6-azidohexyl ester (1.119 g, 4.035 mmol), triphenylphosphine (1.164 g, 4.439 mmol), and water (0.08 ml) in THF was stirred under nitrogen at room temperature. After 144 h, the reaction mixture was diluted with EtOAc (50 ml), dried over Na2SO4, filtered and the filtrate concentrated in vac and dried. The residue was purified by flash chromatography (2×)(alumina, chloroform to 10% MeOH/CHCl3 gradient) to give the desired product as a light yellow oil (0.0796 g, 78%); 1H NMR (400 MHz, DMSO-d6)δ 1.18-1.40 (m, 6H), 1.63-1.71 (m, 2H), 2.50 (t, J=6.4 Hz, 2H), 3.82 (s, 3H), 4.21 (t, J=6.6 Hz, 2H), 7.01-7.06 (m, 2H), 7.87-7.92 (m, 2H); IR (KBr) 3410 (broad), 2940, 1710, 1605, 1510, 1260 cm−; mass spectrum[(+)ESI], m/z 252 (M+H)+.

Provenance & Evidence