palladium diacetate; triethylamine; triphenylphosphine in acetonitrile T=80°C; 24 h;

1: para-bromotoluene With magnesium in diethyl ether 0.333333 h; Heating; 2: ethyl 1,4-dioxaspiro[4,4]nonane-6-carboxylate in diethyl ether 1 h; Heating; 3: With hydrogenchloride in methanol; water 5 h; Heating;

1.1: magnesium / diethyl ether / 0.33 h / Heating 1.2: diethyl ether / 1 h / Heating 1.3: 32 percent / hydrochloric acid / methanol; H2O / 5 h / Heating View Scheme

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C 1.2: tetrahydrofuran / 2 h / -78 °C 2.1: 70 percent / Pd(OAc)2; PPh3; Et3N / acetonitrile / 24 h / 80 °C View Scheme