1: 68 percent / n-BuLi / tetrahydrofuran; hexane / Ambient temperature 2: 86 percent / pyridine / 5 h / Ambient temperature 3: 77 percent / MeSO2Cl, Et3N / diethyl ether / a) 0 deg C, 5 h, b) RT, overnight 4: 75 percent / 20 percent KOH / ethanol / 1 h / Ambient temperature 5: 100 percent / H2 / 5 percent Pd/C / methanol / 48 h / Ambient temperature View Scheme

in n-heptane; dichloromethane 16 h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

sodium periodate 1.) CH2Cl2, heptane, room temp., 16 h, 2.) THF, H2O (1:1), room temp., 2 h; Yield given. Multistep reaction. Yields of byproduct given;

triethylamine 12 h; Ambient temperature;

in tetrahydrofuran T=0 - 20°C;