1: 68 percent / n-butyllithium / hexane; tetrahydrofuran / -78 °C 2: iodine / heptane / 16 h / Heating 3: 82 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.75 h View Scheme

1: NaH / dimethylsulfoxide 2: pyridine 3: 70 percent / Et3N; PPh3 / Pd(OAc)2 / acetonitrile / 17 h / 85 °C View Scheme

1: NaH / dimethylsulfoxide 2: pyridine 3: 70 percent / Et3N; PPh3 / Pd(OAc)2 / acetonitrile / 17 h / 85 °C 4: NaOMe / tetrahydrofuran; methanol View Scheme

1.1: butyllithium / hexane; tetrahydrofuran / 15 - 20 °C 1.2: 78 percent / hexane; tetrahydrofuran / 1 h / 20 °C 2.1: 68.3 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.25 h / 20 °C 3.1: 32 percent / benzyltriethylammonium bromide; NaOH / CHCl3; H2O / 10 h / 60 °C 4.1: sodium methoxide / methanol / 2 h / 20 °C 5.1: 60 percent / sodium ethanethiolate / dimethylformamide / 10 h / 140 °C View Scheme

1.1: butyllithium / hexane; tetrahydrofuran / 15 - 20 °C 1.2: 78 percent / hexane; tetrahydrofuran / 1 h / 20 °C 2.1: 68.3 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.25 h / 20 °C 3.1: 32 percent / benzyltriethylammonium bromide; NaOH / CHCl3; H2O / 10 h / 60 °C 4.1: sodium methoxide / methanol / 2 h / 20 °C 5.1: 60 percent / sodium ethanethiolate / dimethylformamide / 10 h / 140 °C View Scheme

1.1: n-BuLi / tetrahydrofuran / -78 °C 1.2: tetrahydrofuran 2.1: 0.24 g / Bu4NF / tetrahydrofuran / 1 h View Scheme

1.1: n-BuLi / tetrahydrofuran / -78 °C 1.2: tetrahydrofuran 2.1: 0.24 g / Bu4NF / tetrahydrofuran / 1 h View Scheme

sodium hydride in dimethyl sulfoxide Wittig reaction;

1.1: butyllithium / hexane; tetrahydrofuran / 15 - 20 °C 1.2: 78 percent / hexane; tetrahydrofuran / 1 h / 20 °C 2.1: 68.3 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.25 h / 20 °C 3.1: 32 percent / benzyltriethylammonium bromide; NaOH / CHCl3; H2O / 10 h / 60 °C 4.1: sodium methoxide / methanol / 2 h / 20 °C View Scheme