1: 1.) potassium -tert-butoxide / 1.) pentane, 0 deg C, 10 min, 2.) pentane, 20 deg C, 5 h 2: 61 percent / methyllithium / diethyl ether / -70 - 20 °C 3: 1.) lithium, 2.) water / 1.) diethyl ether, 15 deg C, 10 min, 2.) diethyl ether 4: 1.) butyllithium, TMEDA / 1.) hexane, 2.) hexane View Scheme

(i) MeSO2Cl, Et3N, (ii) /BRN= 3587200/, LiCuBr2; Multistep reaction;

1: 1.) CH3Li / 1.) ether, 0 deg C, 1 h, 2.) from 0 deg C to RT, 1 h 2: 1.) <1,3-bis(diphenylphosphino)propane>nickel dichloride (dpppNiCl2) / 1.) ether, benzene, reflux, 15 min, 2.) 80 deg C, 48 h View Scheme

1: 1.) CH3Li / 1.) ether, 0 deg C, 1 h, 2.) from 0 deg C to RT, 1 h 2: 1.) <1,3-bis(diphenylphosphino)propane>nickel dichloride (dpppNiCl2) / 1.) ether, benzene, reflux, 15 min, 2.) 80 deg C, 48 h View Scheme

1: 1.) lithium, 2.) water / 1.) diethyl ether, 15 deg C, 10 min, 2.) diethyl ether 2: 1.) butyllithium, TMEDA / 1.) hexane, 2.) hexane View Scheme

n-butyllithium; N,N,N',N,-tetramethylethylenediamine 1.) hexane, 2.) hexane; Yield given. Multistep reaction. Yields of byproduct given;