hydrogen; palladium on activated charcoal in tetrahydrofuran; methanol

1: 1.) n-butyllithium / 1.) THF, hexane, -100 deg C, 0.5 h, 2.) THF, hexane, from -100 deg C to RT 2: 80 percent / pyridine hydrochloride / 0.17 h / 150 °C 3: 78 percent / H2 / 5percent Pd/C / tetrahydrofuran; methanol / 760 Torr View Scheme

1: 80 percent / pyridine hydrochloride / 0.17 h / 150 °C 2: 78 percent / H2 / 5percent Pd/C / tetrahydrofuran; methanol / 760 Torr View Scheme

1: 1.) n-butyllithium / 1.) THF, hexane, -100 deg C, 0.5 h, 2.) THF, hexane, from -100 deg C to RT 2: 80 percent / pyridine hydrochloride / 0.17 h / 150 °C 3: 78 percent / H2 / 5percent Pd/C / tetrahydrofuran; methanol / 760 Torr View Scheme

1: 82 percent 2: 61 percent / Dibal-H / tetrahydrofuran 3: 65 percent / n-BuLi / tetrahydrofuran / -100 °C 4: 80 percent / pyridine hydrochloride / 0.17 h / 150 °C 5: 95 percent / H2 / Pd/C / methanol; tetrahydrofuran View Scheme

1: 44 percent / MeONa / ethanol; diethyl ether 2: 50 percent / aq. piperidinium acetate 3: 61 percent / PCl5 / 120 °C 4: 82 percent 5: 61 percent / Dibal-H / tetrahydrofuran 6: 65 percent / n-BuLi / tetrahydrofuran / -100 °C 7: 80 percent / pyridine hydrochloride / 0.17 h / 150 °C 8: 95 percent / H2 / Pd/C / methanol; tetrahydrofuran View Scheme