sodium iodide in acetone T=0°C; 1.5 h; Yield given;

1: Et3N / CH2Cl2 / 0.17 h 2: NaI / acetone / 1.5 h / 0 °C View Scheme

1: 77 percent / NaOMe / methanol / 25 deg C -> reflux 2: 1.) NaBH4, 2.) diisobutylaluminum hydride / 1.) methanol, -55 deg C; 2.) toluene, -78 deg C 3: pyridine / CH2Cl2 / 25 °C View Scheme

1: 77 percent / NaOMe / methanol / 25 deg C -> reflux 2: 1.) NaBH4, 2.) diisobutylaluminum hydride / 1.) methanol, -55 deg C; 2.) toluene, -78 deg C 3: pyridine / CH2Cl2 / 25 °C 4: HMPA / 25 °C View Scheme

sodium methylate in methanol 25 deg C -> reflux;

1: 77 percent / NaOMe / methanol / 25 deg C -> reflux 2: 1.) NaBH4, 2.) diisobutylaluminum hydride / 1.) methanol, -55 deg C; 2.) toluene, -78 deg C 3: pyridine / CH2Cl2 / 25 °C 4: HMPA / 25 °C 5: 1.) aq. NaOH / 1.) reflux 6: H2 / Lindlar catalyst 7: pyridine / CH2Cl2 / 0 °C 8: Et3N / -20 °C 9: 1.) NaOMe, MeOH, 2.) Collins reagent, 3.) DBU View Scheme

1: 1.) NaOMe / 1.) MeOH, r.t., 30 min, 2.) MeOH, r.t., 4 h, reflux, 1.5 h 2: NaBH4 / methanol / 0.33 h / -55 °C 3: 1.) DIBAL, 2.) NaBH4 / 1.) toluene, -78 deg C, 1.5 h, 2.) MeOH, -30 deg C, 20 min 4: CH2Cl2; pyridine / 1 h / Ambient temperature 5: 80 percent / 2.5 h / Ambient temperature; HMPT 6: 1.) 10percent NaOH / 1.) EtOH, 16 h, reflux, 2.) ether, 0 deg C 7: 100 percent / quinoline, H2 / Lindlar / methanol / 760 Torr 8: 84 percent / pyridine / CH2Cl2 / 1 h / 0 °C 9: 27 g / Et3N / 0.33 h / -20 °C 10: 1.) NaOMe / 1.) MeOH, 0 deg C, 30 min, 1.5 h, r.t., 2.) ether 11: 20 g / CrO3, Celite / CH2Cl2; pyridine / 0.17 h / 0 °C 12: DBU / toluene / 0.33 h 13: diethyl ether / 1 h / -78 °C 14: CrO3, Celite / CH2Cl2; pyridine / 0.17 h / 0 °C View Scheme