thionyl chloride in chloroform T=45°C; 2 h;

1: 94 percent / Et3N / ethanol; CH2Cl2 / 1 h / -5 - 0 °C 2: 95 percent / 35percent CH3CO3H in AcOH / CH2Cl2 / 1 h / Ambient temperature 3: 100 percent / SOCl2 / CHCl3 / 2 h / 45 °C View Scheme

1: 95 percent / 35percent CH3CO3H in AcOH / CH2Cl2 / 1 h / Ambient temperature 2: 100 percent / SOCl2 / CHCl3 / 2 h / 45 °C View Scheme

1: 37 percent / HCl / 5 h / 50 °C 2: 94 percent / Et3N / ethanol; CH2Cl2 / 1 h / -5 - 0 °C 3: 95 percent / 35percent CH3CO3H in AcOH / CH2Cl2 / 1 h / Ambient temperature 4: 100 percent / SOCl2 / CHCl3 / 2 h / 45 °C View Scheme

1: 94 percent / Et3N / ethanol; CH2Cl2 / 1 h / -5 - 0 °C 2: 95 percent / 35percent CH3CO3H in AcOH / CH2Cl2 / 1 h / Ambient temperature 3: 100 percent / SOCl2 / CHCl3 / 2 h / 45 °C View Scheme

1: 90 percent / NaOEt / ethanol / 1 h / 25 °C 2: 85 percent / CaCl2, NaBH4 / ethanol / 3 h / 25 °C View Scheme