Pentane → (4-Methoxyphenyl)cycloheptane

Participants

Reaction Conditions

Reaction Steps

1.80 M t-BuLi in pentane (0.78 mL, 1.40 mmol) was added at −40° C. to 5.0 mL of a THF solution of 4-methoxyphenylboronic acid pinacol ester (351.2 mg, 1.5 mmol). The reaction mixture was stirred at −40° C. for 30 minutes, and then stirred at 0° C. for 30 minutes. The solvent was removed at 0° C. under reduced pressure. White crystals of the residual lithium t-butyl borate were dissolved in 2.4 mL THF at 0° C. To the resulting solution of lithium t-butyl borate were added undecane (66.2 mg, 0.42 mmol), bromocycloheptane (178.2 mg, 1.01 mmol), a 0.10 M THF solution of magnesium bromide MgBr2 (2.00 mL, 0.20 mmol), and a THF solution (0.60 ml, 0.030 mmol, 3.00 mol %) of an iron chloride.1,2-bis(bis(3,5-trimethylsilylphenyl)phosphino)benzene complex (FeCl2.[3,5-(t-Bu)2]-DPPBz complex). The coupling reaction was performed at 40° C. for 3 hours. The resulting reaction mixture was cooled to 0° C., and 2.0 mL of a saturated aqueous solution of ammonium chloride was subsequently added thereto. The aqueous layer was extracted five times with diethylether. The combined organic extract was filtered using a Florisil pad (100-200 mesh, Nacalai Tesque, Inc.). After thin-layer chromatography (hexane), (4-methoxyphenyl)cycloheptane was obtained as a colorless liquid (0.199 g, yield 97%).

Provenance & Evidence