potassium cyanide in 1,4-dioxane; water 48 h; Ambient temperature;

diethyl cyanophosphonate; triethylamine 1.) DMF, -20 deg C, 10 min, 2.) a) -20 deg C, 30 min, b) ambient temperature, 4 h; Yield given. Multistep reaction;

1: 94 percent / Na, EtOH, H2O / 12 h 2: 67 percent / Na2S*9H2O / methanol / 4 h / Ambient temperature 3: 1.) diethyl cyanophosphonate, 2.) triethylamine / 1.) DMF, -20 deg C, 10 min, 2.) a) -20 deg C, 30 min, b) ambient temperature, 4 h View Scheme

1: 79 percent / triethylamine, isobutyl chloroformate / CH2Cl2 / 0.17 h / -6 °C 2: 1.) NaH / 1.) THF, -20 deg C, 1 h, 2.) THF, -20 deg C to room temperature, 1 h 3: 1.) KH, 2.) MoO5*Py*DMPU / 1.) THF, -20 deg C, 1 h, 2.) a) -20 deg C, 4 h, b) -20 deg C to room temperature View Scheme

1: 67 percent / Na2S*9H2O / methanol / 4 h / Ambient temperature 2: 1.) diethyl cyanophosphonate, 2.) triethylamine / 1.) DMF, -20 deg C, 10 min, 2.) a) -20 deg C, 30 min, b) ambient temperature, 4 h View Scheme

silica gel in ethyl acetate; Petroleum ether Yield given;

1: toluene / 48 h / Irradiation 2: SiO2 / ethyl acetate; light petroleum View Scheme

1: 90 percent / piperidine / 24 h / Heating 2: 95 percent / Na, liq. NH3 / 2 h 3: 79 percent / triethylamine, isobutyl chloroformate / CH2Cl2 / 0.17 h / -6 °C 4: 1.) NaH / 1.) THF, -20 deg C, 1 h, 2.) THF, -20 deg C to room temperature, 1 h 5: 1.) KH, 2.) MoO5*Py*DMPU / 1.) THF, -20 deg C, 1 h, 2.) a) -20 deg C, 4 h, b) -20 deg C to room temperature View Scheme

1: ammonia; sodium / tetrahydrofuran 2: 4-(N,N-dimethlyamino)pyridine; dicyclohexyl-carbodiimide / tetrahydrofuran / 20 °C View Scheme