1: NaH / 1) DMF, 0-60 deg C, 2) 4 h, 60 deg C 2: LiCl*H2O, H2O / 4 h / 160 - 165 °C 3: 90 percent / LAH / diethyl ether 4: 82 percent / Na/NH3 / tetrahydrofuran / 4 h / -78 °C View Scheme

1: NaH / 1) DMF, 0-60 deg C, 2) 4 h, 60 deg C 2: LiCl*H2O, H2O / 4 h / 160 - 165 °C 3: 90 percent / LAH / diethyl ether 4: 82 percent / Na/NH3 / tetrahydrofuran / 4 h / -78 °C 5: 82 percent / pyridine / 1) 0 deg C, 1 h, 2) overnight View Scheme

1: NaH / 1) DMF, 0-60 deg C, 2) 4 h, 60 deg C 2: LiCl*H2O, H2O / 4 h / 160 - 165 °C 3: 90 percent / LAH / diethyl ether 4: 82 percent / Na/NH3 / tetrahydrofuran / 4 h / -78 °C 5: 91 percent / pyridinium chlorochromate (PCC) / CH2Cl2 View Scheme