sodium hydroxide; acetic acid in tetrahydrofuran; water

sodium tetrahydroborate in methanol T=0 - 20°C; 0.15 h;

1.1: lithium aluminium tetrahydride / diethyl ether / 2 h / 0 - 20 °C 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C 2.2: 35 h / 20 °C 3.1: acetic acid / water / 5 h 4.1: sodium tetrahydroborate / methanol / 0.15 h / 0 - 20 °C View Scheme

1: acetic acid / water / 5 h 2: sodium tetrahydroborate / methanol / 0.15 h / 0 - 20 °C View Scheme

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C 1.2: 35 h / 20 °C 2.1: acetic acid / water / 5 h 3.1: sodium tetrahydroborate / methanol / 0.15 h / 0 - 20 °C View Scheme