silphos T=20°C; 0.0833333 h; Neat (no solvent);

1: 91 percent / lithium hydride / diethyl ether / 1 h / Heating 2: 90 percent / pyridine / 24 h / Ambient temperature 3: 55 percent / SnCl4 / benzene / 0.5 h / 0 °C / 1.) 0 deg C, 30 min, 2.) RT, 1.5 h 4: 95 percent / 10percent ethanolic KOH / 6 h / Heating 5: 66 percent / 100percent hydrazine hydrate / bis-(2-hydroxy-ethyl) ether / 30 h / 120 °C 6: 0.4 percent / Raney nickel W-2 / ethanol / 2 h / Heating View Scheme

1: 90 percent / pyridine / 24 h / Ambient temperature 2: 55 percent / SnCl4 / benzene / 0.5 h / 0 °C / 1.) 0 deg C, 30 min, 2.) RT, 1.5 h 3: 95 percent / 10percent ethanolic KOH / 6 h / Heating 4: 66 percent / 100percent hydrazine hydrate / bis-(2-hydroxy-ethyl) ether / 30 h / 120 °C 5: 0.4 percent / Raney nickel W-2 / ethanol / 2 h / Heating View Scheme

1: 84 percent / hydrazine hydrate / bis-(2-hydroxy-ethyl) ether / 0.5 h / 120 °C 2: 91 percent / lithium hydride / diethyl ether / 1 h / Heating 3: 90 percent / pyridine / 24 h / Ambient temperature 4: 55 percent / SnCl4 / benzene / 0.5 h / 0 °C / 1.) 0 deg C, 30 min, 2.) RT, 1.5 h 5: 95 percent / 10percent ethanolic KOH / 6 h / Heating 6: 66 percent / 100percent hydrazine hydrate / bis-(2-hydroxy-ethyl) ether / 30 h / 120 °C 7: 0.4 percent / Raney nickel W-2 / ethanol / 2 h / Heating View Scheme

1: 55 percent / SnCl4 / benzene / 0.5 h / 0 °C / 1.) 0 deg C, 30 min, 2.) RT, 1.5 h 2: 95 percent / 10percent ethanolic KOH / 6 h / Heating 3: 66 percent / 100percent hydrazine hydrate / bis-(2-hydroxy-ethyl) ether / 30 h / 120 °C 4: 0.4 percent / Raney nickel W-2 / ethanol / 2 h / Heating View Scheme

1: 66 percent / 100percent hydrazine hydrate / bis-(2-hydroxy-ethyl) ether / 30 h / 120 °C 2: 0.4 percent / Raney nickel W-2 / ethanol / 2 h / Heating View Scheme

1: 95 percent / 10percent ethanolic KOH / 6 h / Heating 2: 66 percent / 100percent hydrazine hydrate / bis-(2-hydroxy-ethyl) ether / 30 h / 120 °C 3: 0.4 percent / Raney nickel W-2 / ethanol / 2 h / Heating View Scheme

Raney nickel W-2 in ethanol 2 h; Heating; Further byproducts given;