Tetrahydrofuran → 6-(4-Methylphenyl)-1,2,3,4-tetrahydronaphthalene

Participants

Reaction Steps

A THF solution of p-tolylmagnesium bromide (20.0 mL, 20.0 mmol) was placed under vacuum to remove the volatiles. The solvent was replaced with diethoxymethane (20.0 mL). In a separate flask, NiCl2(PCy3)2 (where Cy=cyclohexyl) (355 mg, 0.514 mmol), PCy3 (285 mg, 1.018 mmol), and 6-methoxy-1,2,3,4-tetrahydronaphthalene (1.639 g, 10.11 mmol) was combined in diethoxymethane (2.5 mL). The Grignard reagent was added to this mixture under a nitrogen atmosphere. The resulting solution was stirred 2 minutes at room temperature and then warmed to 90° C. for 15 hours. The reaction was quenched with half saturated aqueous ammonium chloride solution (30 mL) and was extracted with MTBE (3×30 mL). The combined organic layer was dried over MgSO4, filtered and concentrated. The residue was purified by silica gel chromatography (eluted with heptane) to provide 6-(4-methylphenyl)-1,2,3,4-tetrahydronaphthalene (1.43 g, 64% yield)

Provenance & Evidence