1: pentan-3-one; 2-(4-chlorobutyl)-2-ethoxy-1,3-dioxolane With 4,4'-di-tert-butylbiphenyl; lithium in tetrahydrofuran T=-78°C; Barbier-type reaction; 0.5 h; 2: With phosphate buffer T=-78 - 20°C; pH=7; 0.25 h; 3: methanol With toluene-4-sulfonic acid T=20°C;

1.1: HCl / CH2Cl2 / 96 h / 0 °C 2.1: hexane / 48 h / 25 °C 3.1: Li; 4,4'-di-tert-butylbiphenyl / tetrahydrofuran / 0.5 h / -78 °C 3.2: phosphate buffer / tetrahydrofuran / -78 - 25 °C 3.3: 52 percent / PTSA / 12 h / 25 °C View Scheme

1.1: hexane / 48 h / 25 °C 2.1: Li; 4,4'-di-tert-butylbiphenyl / tetrahydrofuran / 0.5 h / -78 °C 2.2: phosphate buffer / tetrahydrofuran / -78 - 25 °C 2.3: 52 percent / PTSA / 12 h / 25 °C View Scheme

2.1: Li; 4,4'-di-tert-butylbiphenyl / tetrahydrofuran / 0.5 h / -78 °C 2.2: phosphate buffer / 0.25 h / -78 - 20 °C / pH 7 2.3: 52 percent / p-toluenesulfonic acid / 20 °C View Scheme