1: molecular sieve, PCC / CH2Cl2 / 2 h / Ambient temperature 2: 1.) t-BuOK / 1.) THF, 20 min; 2.) THF, room temperature, 1 h 3: 30 percent / MCPBA, NaHCO3 / not given 4: 1.) Li, ClPPh2 / 1.) THF; 2.) THF 5: 1.) NaBH4; 2.) silica gel / 1.) EtOH, 0 degC, 3 h; 2.) room temperature, 30 min, benzene View Scheme

Multi-step reaction with 2 steps 1: 90 percent / n-Bu3N, PPh3 / Pd(OAc)2 / toluene / 48 h / 110 °C / 3800 Torr2: 65 percent / HCl / methanol / 12 h / 50 °C  

With  PPC on alumina in  dichloromethane 48 h;