Diethyl Ether → 6-Methoxy-1,1,4,7-tetramethyl-1,2-dihydronaphthalene

Participants

Reaction Steps

General Procedure A CeCl3 7 H2O (1.28 g, 3.4 mmol) was heated in an oil bath to 140-150° C. under high vacuum without stirring for 2 h, and then with stirring for 2 h. Argon was then introduced, and the flask was cooled to room temperature. Tetrahydrofuran (10 mL) was added, and the resulting slurry solution was stirred at room temperature under the argon atmosphere for 3 h. A solution of 7-methoxy-4,4,6-trimethyl-3,4-dihydro-2H-naphthalen-1-one (Compound 6, 0.53 g, 2.3 mmol) and 5 mL of tetrahydrofuran was added, and the reaction mixture was stirred for 1 h, then cooled to 0° C. A solution of 3 M MeMgBr in diethyl ether (1.2 mL, 3.4 mmol) was added, and the ice bath was removed. After 1 h, the reaction was poured into concentrated sulfuric acid in ice, extracted with ethyl acetate, washed with IN NaHCO3, brine, dried over MgSO4, and filtered. The solvent was removed to give 0.42 g (80%) of the title compound as an orange oil.

Provenance & Evidence