1: 92 percent / Mg / tetrahydrofuran 2: 1) potassium tert-butoxide 2) HCl aq. / 1) DMF, 40 deg C 2) THF 3: 1) LiAlH4 2) KHSO4 / 1) Et2O 2) heating View Scheme

1: KHMDS / tetrahydrofuran; toluene / 0.17 h / -78 °C 2: (Bu3Sn)(Bu)CuLi*CN / tetrahydrofuran / -78 °C View Scheme

thionyl chloride; Zinc chloride

1: 92 percent / 1) Na, 2) HMPT / tetrahydrofuran / 1) 12 h, reflux, 2) 3 h, reflux 2: 98 percent / diethyl ether; methanol 3: 71 percent / O3 / CH2Cl2 / -78 °C 4: 85 percent / LiAlH4 / diethyl ether / 12 h / Heating 5: 76 percent / PBr3 / petroleum ether; pyridine / Ambient temperature View Scheme

1: 92 percent / 1) Na, 2) HMPT / tetrahydrofuran / 1) 12 h, reflux, 2) 3 h, reflux 2: 98 percent / diethyl ether; methanol 3: 71 percent / O3 / CH2Cl2 / -78 °C 4: 85 percent / LiAlH4 / diethyl ether / 12 h / Heating View Scheme