sodium hydroxide T=50°C;

1: 95 percent / Zn powder / acetic acid; tetrahydrofuran / 4 h / 55 - 65 °C 2: 78 percent / diethyl phosphorocyanidate; Et3N / tetrahydrofuran / 2 h / 20 °C 3: 93 percent / CH2Cl2 / Heating 4: 95 percent / BuLi / hexane; tetrahydrofuran / 1 h / -15 °C 5: 82 percent / NaI; TMSCl / acetonitrile / 20 °C 6: 92 percent / LHMDS / tetrahydrofuran; hexane / 2 h / 20 °C 7: 685 mg / DMD / acetone / 0.75 h / -78 - -30 °C 8: BF3*OEt2 / CH2Cl2 / -50 - 5 °C 9: 75 percent / SOCl2; Et3N / pyridine; CHCl3 / -78 - 20 °C 10: 51 percent / H2 / 10 percent Pd-C / acetic acid / 48 h / 2280 Torr View Scheme