1: mesyl-Cl, LiBr / acetone View Scheme

lithium; iron nitrate (III) 1) NH3(l)/THF, 1 h, 2) THF, 4 h; Yield given. Multistep reaction;

Yield given;

1: 80 percent / LiAlH4 / tetrahydrofuran / 1) rt, overnight, 2) reflux, 8 h 2: 78 percent / PBr3, pyridine / diethyl ether / 1) rt, 2 h, 2) reflux, 2.5 h 3: 1) magnesium / 3) Li2CuCl4 / 1) THF, a) rt, b) 30 deg C, 3 h, 2) THF, - 5 deg C, 30 min, 3) a) -5 to -10 deg C, 4 h, b) overnight 4: 67 percent / p-toluenesulphonic acid / methanol / 2 h / Heating View Scheme

1: 80 percent / LiAlH4 / tetrahydrofuran / 1) rt, overnight, 2) reflux, 8 h 2: 78 percent / PBr3, pyridine / diethyl ether / 1) rt, 2 h, 2) reflux, 2.5 h 3: 1) magnesium / 3) Li2CuCl4 / 1) THF, a) rt, b) 30 deg C, 3 h, 2) THF, - 5 deg C, 30 min, 3) a) -5 to -10 deg C, 4 h, b) overnight 4: 67 percent / p-toluenesulphonic acid / methanol / 2 h / Heating 5: 70 percent / pyridine / neat (no solvent) / 24 h / Ambient temperature View Scheme