sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride in dichloromethane 0.25 h; Ambient temperature;

in tetrahydrofuran T=0°C; 0.0333333 h;

lithium aluminium tetrahydride in tetrahydrofuran Heating;

in tetrahydrofuran T=20°C; 3 h;

1: H2 / PtO2 / ethanol / 10 h / 2792.6 Torr 2: 65 percent / 50percent aq. NaOH, benzyltriethylammonium chloride / CH2Cl2 / 0.25 h / Ambient temperature View Scheme

1: 1 g / POCl3, P2O5 / 2 h / Heating 2: H2 / PtO2 / ethanol / 10 h / 2792.6 Torr 3: 65 percent / 50percent aq. NaOH, benzyltriethylammonium chloride / CH2Cl2 / 0.25 h / Ambient temperature View Scheme

1: 92 percent / 10percent aq. NaOH / CH2Cl2 / 0.25 h 2: 1 g / POCl3, P2O5 / 2 h / Heating 3: H2 / PtO2 / ethanol / 10 h / 2792.6 Torr 4: 65 percent / 50percent aq. NaOH, benzyltriethylammonium chloride / CH2Cl2 / 0.25 h / Ambient temperature View Scheme

1: 92 percent / 10percent aq. NaOH / CH2Cl2 / 0.25 h 2: 1 g / POCl3, P2O5 / 2 h / Heating 3: H2 / PtO2 / ethanol / 10 h / 2792.6 Torr 4: 65 percent / 50percent aq. NaOH, benzyltriethylammonium chloride / CH2Cl2 / 0.25 h / Ambient temperature View Scheme

1: 1) PH3(+)*BF4(1-) / 1) MeCN, 20 deg C, 3 h, 2) MeCN, 20 deg C, 20 min 2: 100 percent / tetrahydrofuran / 0.03 h / 0 °C View Scheme

1: (isoPrO)4Ti / 3 h / 80 °C 2: NaBH4 / methanol / 1 h / Ambient temperature 3: 98 percent / Ac2O / 1 h / 70 °C 4: 97 percent / NaIO4 / H2O; methanol / Ambient temperature 5: 1.) TFAA; 2.) BF3*Et2O / 1.) benzene, RT, 1 h; 2.) benzene, RT, 1 h 6: 89 percent / NaBH4, NiCl2*6H2O / methanol; tetrahydrofuran / 0.5 h / Ambient temperature 7: 90 percent / LiAlH4 / tetrahydrofuran / Heating View Scheme