palladium in methanol

1.1: i-Pr2NH; n-BuLi / tetrahydrofuran; hexane / 0.67 h / -75 °C 1.2: 77 percent / tetrahydrofuran; hexane / 20 h / -75 - 15 °C 2.1: O3 / methanol / -78 °C 2.2: Me2S / methanol / -78 - 0 °C 2.3: 59 percent / AcOH; NaCNBH3 / methanol; tetrahydrofuran / 72 h / 20 °C 3.1: 85 percent / LiAlH4 / tetrahydrofuran / 24 h / Heating 4.1: 13.9 g / H2 / Pd(OH)2/C / methanol / 64 h / 20 °C / 1551.44 Torr View Scheme