thionyl chloride 2 - 4 h; Heating / reflux; Product distribution / selectivity;

1: 40 percent / HNO3 / acetic anhydride / -25 °C 2: SOCl2 / tetrahydrofuran / 1 h / Heating View Scheme

1: 79 percent / NaOH / ethanol; dioxane / 2 h / Ambient temperature 2: tionyl chloride / 3 h / Heating View Scheme

1: aq. NaOH / tetrahydrofuran; methanol 2: thionyl chloride / 2 h / 60 °C View Scheme

thionyl chloride in acetonitrile Heating;

1: Hunig's base / tetrahydrofuran / -20 - 20 °C 2: 1.) H2, 2.) HCl / 10percent Pd/C / 1.) methanol, 40 deg C, 1 atm, 2.) isopropanol, -30 deg C 3: 64 percent / 1,8-bis(dimethylamino)naphthalene, dicyclohexylcarbodiimide / tetrahydrofuran; dimethylformamide / 3 h / Ambient temperature 4: 1.) HCl, 2.) NH3 / 1.) EtOH, RT, 1.5 h, 2.) EtOH, 1 h, RT 5: 70 percent / H2 / 10percent Pd/C / methanol / 40 °C 6: methanol; tetrahydrofuran / 0.5 h / -40 °C View Scheme

N-ethyl-N,N-diisopropylamine in tetrahydrofuran T=-20 - 20°C; Yield given;

1: 7.22 g / Huenig's base / tetrahydrofuran / -20 - 20 °C 2: H2 / Pd/C / methanol View Scheme

triethylamine in dichloromethane