Triethylsilane → 6-Bromo-1,1-dimethyl-1,2,3,4-tetrahydronaphthalene

Participants

Reaction Steps

To a solution of 7-bromo-4,4-dimethyl-3,4-dihydro-2H-naphthalen-1-one (prepared according to the procedures published in Journal of Medicinal Chemistry 1995, 38, 4764-7) (525 mg, 2.08 mmol) in 5 mL of trifluoroacetic acid (TFA) was added triethylsilane (2.41 g, 20.80 mmol). The mixture was then heated at reflux for 8 h. After cooling to room temperature, the reaction was quenched with 20 mL of ice-water mixture, extracted with diethyl ether (3×5 mL), washed with brine (1×5 mL), dried (MgSO4) and concentrated at reduced pressure. Purification by flash chromatography (hexane) afforded the title compound (445 mg, 90% yield) as a light yellow oil:

Provenance & Evidence