1: 78 percent / DIBAH / CH2Cl2; petroleum ether / -70 - 25 °C 2: 1) LiAlH4, 2) NEt3 / 1) THF, 0 deg C to r.t., 2) CH3CN, -15 deg C 3: 79 percent / PPh3, DEAD / toluene / Ambient temperature 4: 78 percent / BTAC / CH2Cl2 / Ambient temperature 5: 58 percent / Na / liquid ammonia / -70 °C View Scheme

Multi-step reaction with 4 steps 1: 78 percent / DIBAH / CH2Cl2; petroleum ether / -70 - 25 °C2: 1) LiAlH4, 2) NEt3 / 1) THF, 0 deg C to r.t., 2) CH3CN, -15 deg C3: 79 percent / PPh3, DEAD / toluene / Ambient temperature4: 78 percent / BTAC / CH2Cl2 / Ambient temperature