Triethylamine → 5-Phenoxy-1,2,3,4-tetrahydroquinoline

Participants

Reaction Steps

To a solution of 0.15 g (1.01 mmol) 1,2,3,4-tetrahydro-quinolin-5-ol in 10 ml dichloromethane were added 0.17 g (1.40 mmol) phenylboronic acid, 0.25 g (1.36 mmol) copper(II) acetate, a spatula end of 4 Å molecular sieves and 0.57 ml (4.52 mmol) triethylamine. The reaction mixture was stirred at room temperature for 72 h and then filtered through celite, washing with dichloromethane. The filtrate was concentrated in vacuo and the residue was purified by flash chromatography (silica gel, ethyl acetate/heptane gradient) to afford 34 mg (17%) of the title compound as a pink oil. MS (ISP): 226.3 ([M+H]+).

Provenance & Evidence