potassium carbonate in water; acetone 48 h; Ambient temperature;

1: 1) LiAlH4, 2) 2N HCl, air / 1) Et2O, reflux, 2 h, 2) overnight 2: 79 percent / SOCl2, pyridine / CH2Cl2 / 4 h / Ambient temperature 3: 30 percent / K2CO3 / acetone; H2O / 48 h / Ambient temperature View Scheme

1: 79 percent / SOCl2, pyridine / CH2Cl2 / 4 h / Ambient temperature 2: 30 percent / K2CO3 / acetone; H2O / 48 h / Ambient temperature View Scheme

1: 1) 6N HCl, 3M NaNO2 / 1) 1 h, 2) H2O 2: 1) LiAlH4, 2) 2N HCl, air / 1) Et2O, reflux, 2 h, 2) overnight 3: 79 percent / SOCl2, pyridine / CH2Cl2 / 4 h / Ambient temperature 4: 30 percent / K2CO3 / acetone; H2O / 48 h / Ambient temperature View Scheme