1: 1.) n-BuLi / 1.) THF, hexane, -23 deg C, 2 h, 2.) THF, hexane, -23 deg C, 3 h 2: NH3 / tetrahydrofuran; hexane / 0.25 h / 5 °C 3: 1.) O3, 2.) H2O2 / 1.) Me2CO, water, 5 deg C, 30 min, 2.) Me2CO, water, 20 deg C, overnight View Scheme

1: POCl3 / CH2Cl2 / 3 h / -10 °C 2: Et3N / CH2Cl2 / Ambient temperature 3: 1.) O3, 2.) H2O2 / 1.) Me2CO, water, 5 deg C, 30 min, 2.) Me2CO, water, 20 deg C, overnight View Scheme

thionyl chloride

1: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere 2: Grubb's 2nd generation catalyst / 1,2-dichloro-ethane / Inert atmosphere; Reflux 3: palladium 10 on activated carbon; hydrogen / methanol / 1500.15 Torr View Scheme