triethylamine in methanol; chloroform T=0°C; 1 h;

1: 97 percent / LiAlH4, AlCl3 / diethyl ether / 2 h / 25 °C 2: 83 percent / H2, NH4OH / 10percent Pd/C / ethanol / 2 h / 0 °C / 760 Torr 3: 58 percent / Et3N / methanol; CHCl3 / 1 h / 0 °C View Scheme

1: 83 percent / H2, NH4OH / 10percent Pd/C / ethanol / 2 h / 0 °C / 760 Torr 2: 58 percent / Et3N / methanol; CHCl3 / 1 h / 0 °C View Scheme

1: 97 percent / K2CO3, KI / dimethylformamide / 2 h / 25 °C 2: 97 percent / LiAlH4, AlCl3 / diethyl ether / 2 h / 25 °C 3: 83 percent / H2, NH4OH / 10percent Pd/C / ethanol / 2 h / 0 °C / 760 Torr 4: 58 percent / Et3N / methanol; CHCl3 / 1 h / 0 °C View Scheme

water; sodium acetate; acetic acid pH=3 - 5; Reactivity;