4-(N,N-dimethlyamino)pyridine; triethylamine in tetrahydrofuran T=0 - 20°C; Inert atmosphere; regioselective reaction;

1: butyl 2-(trityloxy)acetate With diisobutylaluminium hydride in dichloromethane; cyclohexane T=-78°C; 0.333333 h; 2: vinyl-magnesium chloride in tetrahydrofuran; dichloromethane; cyclohexane T=-78 - 20°C;

n-butyllithium in tetrahydrofuran 3 h; Ambient temperature; Yields of byproduct given;

1.1: pyridine / 18 h / 65 °C 2.1: diisobutylaluminium hydride / dichloromethane; cyclohexane / 0.33 h / -78 °C 2.2: -78 - 20 °C View Scheme

1: 74 percent / m-CPBA / CH2Cl2 / 3 h / Ambient temperature 2: n-BuLi / tetrahydrofuran / 3 h / Ambient temperature View Scheme