1: 1.) butyllithium, hexamethylphosphoric triamide / 1.) hexane, 0 deg C, 10 min, 2.) hexane, 4 h 2: 20 g / H2 / 10percent palladium on charcoal / ethanol / 16 h / 760 Torr 3: tin(IV) chloride / benzene / 0.25 h View Scheme

1: 1.) butyllithium, hexamethylphosphoric triamide / 1.) hexane, 0 deg C, 10 min, 2.) hexane, 4 h 2: 20 g / H2 / 10percent palladium on charcoal / ethanol / 16 h / 760 Torr 3: tin(IV) chloride / benzene / 0.25 h View Scheme

1: 20 g / H2 / 10percent palladium on charcoal / ethanol / 16 h / 760 Torr 2: tin(IV) chloride / benzene / 0.25 h View Scheme

tin(IV) chloride in benzene 3 h; Heating;

tin(IV) chloride in benzene 0.25 h; Yield given;