sodium tetrahydroborate; triethylamine in methanol T=0°C; 2 h;

1: 75 percent / ethyl acetate / 72 h / 120 °C 2: 60 percent / NaBH4, Et3N / methanol / 1 h / 0 °C View Scheme

1: 72.25 percent / phosphorus tribromide / benzene / 2 h / Heating 2: 75 percent / ethyl acetate / 72 h / 120 °C 3: 60 percent / NaBH4, Et3N / methanol / 1 h / 0 °C View Scheme

1: 94 percent / sulphuric acid / 24 h / 25 °C 2: 88 percent / lithium aluminium hydride / diethyl ether / 1 h / 30 °C 3: 72.25 percent / phosphorus tribromide / benzene / 2 h / Heating 4: 75 percent / ethyl acetate / 72 h / 120 °C 5: 60 percent / NaBH4, Et3N / methanol / 1 h / 0 °C View Scheme

1: 88 percent / lithium aluminium hydride / diethyl ether / 1 h / 30 °C 2: 72.25 percent / phosphorus tribromide / benzene / 2 h / Heating 3: 75 percent / ethyl acetate / 72 h / 120 °C 4: 60 percent / NaBH4, Et3N / methanol / 1 h / 0 °C View Scheme

1: 75 percent / ethyl acetate / 72 h / 120 °C 2: 60 percent / NaBH4, Et3N / methanol / 1 h / 0 °C View Scheme

1: NaH / tetrahydrofuran / 24 h / 30 °C 2: H2SO4 / 21 h / 30 °C 3: LAH / diethyl ether / 2 h / 30 °C 4: PBr3 / benzene / 5 h / Heating 5: 80 percent / ethyl acetate / 120 °C 6: 65 percent / NaBH4, Et3N / methanol / 2 h / 0 °C View Scheme