1: 73 percent / NaH / benzene; 2-methyl-propan-2-ol / 6 h / Heating 2: 1.) NaH, 2.) NaI / 1.) benzene, DMF, 30 min, 2.) 20 deg C, 2 h 3: trifluoroacetic acid / 3 h 4: toluene; methanol / 4 h / Heating View Scheme

1: 73 percent / NaH / benzene; 2-methyl-propan-2-ol / 6 h / Heating 2: 1.) NaH, 2.) NaI / 1.) benzene, DMF, 30 min, 2.) 20 deg C, 2 h 3: trifluoroacetic acid / 3 h 4: toluene; methanol / 4 h / Heating View Scheme

1.1: 84 percent / NaH / toluene; 2-methyl-propan-2-ol / 3 h / 100 °C 2.1: NaH / tetrahydrofuran / 0.33 h 2.2: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C 2.3: 92 percent / tetrahydrofuran; hexane / -78 - 0 °C 3.1: 93 percent / NaBH4 / ethanol / 1 h / 0 °C 4.1: 87 percent / PPh3; DIAD / tetrahydrofuran / 20 °C View Scheme

sodium hydride in toluene; tert-butyl alcohol T=100°C; 3 h;

copper dichloride; lithium diisopropyl amide 1.) THF, -78 deg C, 15 min, 2.) THF, -78 deg C, 3 h; Yield given. Multistep reaction. Yields of byproduct given;

1: 73 percent / NaH / benzene; 2-methyl-propan-2-ol / 6 h / Heating 2: 1.) NaH, 2.) NaI / 1.) benzene, DMF, 30 min, 2.) 20 deg C, 2 h 3: trifluoroacetic acid / 3 h 4: toluene / 4 h / Heating View Scheme

1: 73 percent / NaH / benzene; 2-methyl-propan-2-ol / 6 h / Heating 2: 1.) NaH, 2.) NaI / 1.) benzene, DMF, 30 min, 2.) 20 deg C, 2 h 3: trifluoroacetic acid / 3 h View Scheme

1.1: NaH; t-BuOH / toluene / Heating 2.1: NaH / tetrahydrofuran / 0.5 h / 0 °C 2.2: 91 percent / n-BuLi / tetrahydrofuran / 0.5 h / -78 °C 3.1: 91 percent / NaBH4 / ethanol / 0.75 h / 0 °C 4.1: pyridine / 0 °C 5.1: 73 percent / DBU / CH2Cl2 / 4 h / 0 °C View Scheme