pyridine in diethyl ether

1: 1.) 2M BuLi / 1.) hexane, HMPT, 0 deg C, 30 min, 2.)THF, r. t., 12 h 2: p-TsOH / methanol / 2 h / Heating 3: 95 percent / H2, quinoline / Lindlar catalyst / pentane / 1 h / -10 °C 4: 95 percent / pyridine / diethyl ether View Scheme

1: p-TsOH / diethyl ether 2: 1.) 2M BuLi / 1.) hexane, HMPT, 0 deg C, 30 min, 2.)THF, r. t., 12 h 3: p-TsOH / methanol / 2 h / Heating 4: 95 percent / H2, quinoline / Lindlar catalyst / pentane / 1 h / -10 °C 5: 95 percent / pyridine / diethyl ether View Scheme

1: 95 percent / H2, quinoline / Lindlar catalyst / pentane / 1 h / -10 °C 2: 95 percent / pyridine / diethyl ether View Scheme

1: 91 percent / acetonitrile 2: 63 percent / DMSO, NaH / tetrahydrofuran / 0.5 h 3: pyridine View Scheme

1: 63 percent / DMSO, NaH / tetrahydrofuran / 0.5 h 2: pyridine View Scheme

pyridine Yield given. Yields of byproduct given. Title compound not separated from byproducts;