1: 94 percent / bis(triphenylphosphine)nickel dichloride, methylmagnesium iodide / benzene; diethyl ether / 15 h / Heating 2: 1.) methylmagnesium bromide / 1.) Et2O, benzene, 0 deg C, 30 min, 2.) 2.5 h View Scheme

1: 34 percent / diethyl ether / 2 h / Ambient temperature 2: 8 percent / lithium aluminum hydride / tetrahydrofuran / a) 0 deg C, 0.5 h, b) RT, 1 h View Scheme

1: 1.) tetra-n-butylammonium bisulfate, 50percent KOH / 1.) benzene, 5 min, 2.) 2 h 2: 1.) a) tert-butyllithium, b) cuprous cyanide / 1.) pentane, THF-Et2O 3:1 a) -95 deg C, 6 min b) -90 deg C, 3 min, 2.) a) -95 deg C, 0.5 h, b) -78 deg C, 1 h, c) RT, 14 h 3: 95 percent / sodium amalgam, disodium hydrogenphosphate / methanol / 1 h / Ambient temperature View Scheme

1: 1.) a) tert-butyllithium, b) cuprous cyanide / 1.) pentane, THF-Et2O 3:1 a) -95 deg C, 6 min b) -90 deg C, 3 min, 2.) a) -95 deg C, 0.5 h, b) -78 deg C, 1 h, c) RT, 14 h 2: 95 percent / sodium amalgam, disodium hydrogenphosphate / methanol / 1 h / Ambient temperature View Scheme

bis(η3-allyl-μ-chloropalladium(II)); lithium carbonate; triphenylphosphine in dichloromethane Tsuji-Trost reaction; Title compound not separated from byproducts;

1: NBS / tetrahydrofuran / -78 °C View Scheme

1: 92 percent / potassium tert-butoxide / tetrahydrofuran / 1 h / Ambient temperature 2: 8 percent / lithium aluminum hydride / tetrahydrofuran / a) 0 deg C, 0.5 h, b) RT, 1 h View Scheme

boron trifluoride diethyl etherate in N,N-dimethyl-formamide 13 h; Ambient temperature; Yield given. Yields of byproduct given;

methylmagnesium bromide 1.) Et2O, benzene, 0 deg C, 30 min, 2.) 2.5 h; Yield given. Multistep reaction. Further byproducts given. Yields of byproduct given. Title compound not separated from byproducts;

Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;