1: 1) n-BuLi / 1) ether, hexane, -78 deg C, 2) THF, a) -78 deg c, 1 h, b) -78 deg C to -20 deg C, 1 h 2: thionyl chloride, pyridine / 2 h / 0 °C 3: H2 / 10percent Pd/C / ethyl acetate / 3 h / 760 Torr / Ambient temperature View Scheme

1: 1) n-BuLi / 1) ether, hexane, -78 deg C, 2) THF, a) -78 deg c, 1 h, b) -78 deg C to -20 deg C, 1 h 2: thionyl chloride, pyridine / 2 h / 0 °C 3: H2 / 10percent Pd/C / ethyl acetate / 3 h / 760 Torr / Ambient temperature View Scheme