6-Methoxy-alpha-tetralone → HCID 11831424, compound

Participants

Reaction Steps

A solution of phenylmagnesium bromide in diethyl ether (3.0 M, 23 mL, 69 mmol) was added dropwise to a solution of 6-methoxy-1,2,3,4-tetrahydronaphthalen-1-one 27 (10.0 g, 56.7 mmol) in diethyl ether (100 mL) at room temperature. The reaction mixture was heated at reflux for 1.5 h. An additional portion of phenylmagnesium bromide solution (10 mL, 60 mmol) was added to the cooled reaction mixture, and the resultant mixture was heated at reflux for an additional 2.5 h. The cooled mixture was poured into a saturated solution of ammonium chloride (200 mL), and stirred for 15 min. The organic layer was separated, washed with a saturated solution of sodium chloride, and dried over magnesium sulfate. The solvent was evaporated in vacuo, and the resultant oil was treated with a solution of sulfuric acid (8 mL) in acetic acid (30 mL) at room temperature for 1.5 h. Ice water (300 mL) was added to the solution, and the product was extracted into dichloromethane (200 mL), washed with water, and a saturated aqueous solution of sodium bicarbonate, and dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was purified by medium pressure chromatography using ethyl acetate 0 to 3% in hexanes as the eluent, to give the 6-methoxy-1-phenyl-3,4-dihydronaphthalene 28 in two crops 4.0 g (29%) and an impure fraction 5.02 g (37%) as an oil.

Provenance & Evidence