potassium tert-butylate in N,N-dimethyl-formamide; pentane T=-78 - -60°C; 4 h;

1: tert-butyl alcohol With sodium hydride; potassium iodide in tetrahydrofuran T=0°C; 0.25 h; 2: chloroacetic acid in tetrahydrofuran 24 h; Heating; Further stages.;

potassium carbonate in methanol 17 h; Heating;

in tetrahydrofuran 1.5 h; Reflux;

sulfuric acid; mercuric sulphate in diethyl ether; pentane 2.75 h; Ambient temperature;

1: Mg, 1,2-dibromoethane / tetrahydrofuran / Irradiation; 1.) 50 deg C, 45 min then, 2.) 40 deg C, 30 min then room temp. 2: 1.) Br2; 2.) tBuOK / 1.) pentane, -15 deg C; 2.) 0 deg C, 120 min 3: 92 percent / NaNH2 in liq NH3 / pentane; diethyl ether / 0.3 h 4: 59 percent / HgSO4, 6NH2SO4 / diethyl ether; pentane / 2.75 h / Ambient temperature View Scheme

1: 97 percent / PCl5 / CCl4 / 1.5 h / -12 °C 2: Mg, 1,2-dibromoethane / tetrahydrofuran / Irradiation; 1.) 50 deg C, 45 min then, 2.) 40 deg C, 30 min then room temp. 3: 1.) Br2; 2.) tBuOK / 1.) pentane, -15 deg C; 2.) 0 deg C, 120 min 4: 92 percent / NaNH2 in liq NH3 / pentane; diethyl ether / 0.3 h 5: 59 percent / HgSO4, 6NH2SO4 / diethyl ether; pentane / 2.75 h / Ambient temperature View Scheme

1: CH2Cl2 / 5 h / Ambient temperature 2: Mg, 1,2-dibromoethane / tetrahydrofuran / Irradiation; 1.) 50 deg C, 45 min then, 2.) 40 deg C, 30 min then room temp. 3: 1.) Br2; 2.) tBuOK / 1.) pentane, -15 deg C; 2.) 0 deg C, 120 min 4: 92 percent / NaNH2 in liq NH3 / pentane; diethyl ether / 0.3 h 5: 59 percent / HgSO4, 6NH2SO4 / diethyl ether; pentane / 2.75 h / Ambient temperature View Scheme

potassium hydroxide in ethanol 18 h;

1: 1.) Br2; 2.) tBuOK / 1.) pentane, -15 deg C; 2.) 0 deg C, 120 min 2: 92 percent / NaNH2 in liq NH3 / pentane; diethyl ether / 0.3 h 3: 59 percent / HgSO4, 6NH2SO4 / diethyl ether; pentane / 2.75 h / Ambient temperature View Scheme