sodium hydride in diethyl ether

1: 80 percent / acetone / 10 h / Irradiation 2: 95 percent / 520 °C / 0.01 Torr 3: 94 percent / H2 / Pd/C / ethanol / 6 h 4: 90 percent / LDA; THF / hexamethylphosphoric acid triamide / 5 h / -78 - 20 °C 5: 88 percent / lithium aluminium hydride / tetrahydrofuran / Heating View Scheme

1: 80 percent / acetone / 10 h / Irradiation 2: 95 percent / 520 °C / 0.01 Torr 3: 94 percent / H2 / Pd/C / ethanol / 6 h 4: 90 percent / LDA; THF / hexamethylphosphoric acid triamide / 5 h / -78 - 20 °C 5: 88 percent / lithium aluminium hydride / tetrahydrofuran / Heating 6: 96 percent / pyridine; DMAP / 24 h 7: 70 percent / sodium cyanoborohydride / hexamethylphosphoric acid triamide / 24 h / 130 °C 8: 18 percent / CrO3; glacial CH3COOH / H2O / 5 h View Scheme