Hydroquinone → (4aS,8aS)-2-Benzoyl-4a-(3-methoxyphenyl)octahydroisoquinolin-6(2H)-one

Participants

Reaction Steps

278 ml. of 2.2 N butyl lithium solution (612 mmol) are added to a mixture of 600 ml of absolute tetrahydrofuran, 112.2 g (600 mmol) of 3-bromoanisole and 661 mg (6 mmol) of hydroquinone at -65° under nitrogen. The resulting mixture is kept at -50° for 30 minutes, treated with 57.13 g (0.3 mol) of copper (I) iodide, stirred for 1 hour at -43°, and treated with 51.06 g (0.2 mol) of 1,3,4,7,8,8a-hexahydro-2-benzoyl-6(2H)-isoquinolinone. The mixture is allowed to warm to 0° over 2 hours and kept at 0° for 16 hours. 1.2 liters of water and 79.28 g (0.6 mol) of ammonium sulphate are added to the mixture which is then extracted with toluene. The organic extracts are evaporated to yield an oil which is chromatographed on silicagel using ethyl acetate as eluant. The product, 2-benzoyl-octahydro-4a-(3-methoxyphenyl)-cis-6(2H)-iso-quinolinone is obtained as colourless crystals from methanol; M.Pt. 78°.

Provenance & Evidence