1.1: (Me3Si)2NK / tetrahydrofuran 1.2: 64 percent / tetrahydrofuran 2.1: CuCN / diethyl ether / 0.08 h / 0 °C 2.2: 91 percent / diethyl ether; tetrahydrofuran / 2.5 h / -78 °C 3.1: DIBAL-H / toluene View Scheme

1: 53 percent / (Me3Si)2NK / tetrahydrofuran; toluene / 1.) -78 deg C, 2. ) -78 deg C to room temp., overnight 2: 77 percent / Ph3As, bis(benzonitrile)palladium(II) chloride, CuI / various solvent(s) / 18 h / 100 °C View Scheme

1: KN(SiMe3)2 / tetrahydrofuran; toluene 2: 93 percent / CuI; Ph3As; bis(benzonitrile)palladium(II) chloride / 1-methyl-pyrrolidin-2-one / 18 h / 100 °C 3: 65 percent / DIBAL-H / toluene / 1 h / -78 °C View Scheme