titanium(IV) isopropylate in tetrahydrofuran; diethyl ether T=20°C; Kulinkovich reaction; 18 h;

1.1: Et3N; DMAP / CH2Cl2 / 4 h / 20 °C 2.1: 57.0 g / oxone / tetrahydrofuran; H2O / 8 h / 20 °C 3.1: SOCl2 / 1,2-dichloro-ethane / 1 h / Heating 3.2: NCS; aq. HCl / 1,2-dichloro-ethane / 12 h / 90 °C 3.3: 93 percent / 1,2-dichloro-ethane / 1 h / 20 °C 4.1: 99 percent / Et3N / CH2Cl2 / 8 h / 0 °C View Scheme

1: Et3N; DMAP / CH2Cl2 / 4 h / 20 °C 2: 57.0 g / oxone / tetrahydrofuran; H2O / 8 h / 20 °C View Scheme

1: Et3N; DMAP / CH2Cl2 / 4 h / 20 °C 2: 57.0 g / oxone / tetrahydrofuran; H2O / 8 h / 20 °C 3: 83 percent / p-TsOH hydrate / toluene / 6 h / Heating View Scheme