1: 1.) butyllithium / 1.) THF, hexane, -70 deg C, 15 min, 2.) a) -70 deg C, 5 h, b) from -70 deg to RT, 1.5 h, c) RT, 15 h 2: 90 percent / H2 / 2percent Pd-C / hexane / 120 h / Ambient temperature 3: 99.9 percent / KOH / methanol; H2O / 1.) 50 deg C, 6 h, 2.) RT, 15 h View Scheme

1: 1.) butyllithium / 1.) THF, hexane, -70 deg C, 15 min, 2.) a) -70 deg C, 5 h, b) from -70 deg to RT, 1.5 h, c) RT, 15 h 2: 90 percent / H2 / 2percent Pd-C / hexane / 120 h / Ambient temperature 3: 69 percent / lithium aluminum hydride / diethyl ether / 1.) reflux, 5 h, 2.) from 20 deg C to 25 deg C, 15 h View Scheme

1: 1.) butyllithium / 1.) THF, hexane, -70 deg C, 15 min, 2.) a) -70 deg C, 5 h, b) from -70 deg to RT, 1.5 h, c) RT, 15 h 2: 90 percent / H2 / 2percent Pd-C / hexane / 120 h / Ambient temperature View Scheme

n-butyllithium in tetrahydrofuran T=-30°C;