1: propan-2-ol / Heating 2: aq. NaBH4 / methanol 3: propan-2-ol / Heating 4: (i) Ag2O, MeOH, (ii) (pyrolysis), (iii) H2, Pd-C, AcOEt View Scheme

in isopropyl alcohol Heating;

potassium tert-butylate in tetrahydrofuran T=20°C; 2 h;

1.1: 40 percent / potassium tert-butoxide / tetrahydrofuran / 2 h / 20 °C 2.1: potassium tert-butoxide / tetrahydrofuran / 0.17 h / 0 °C 2.2: 86 percent / tetrahydrofuran / 0 °C 3.1: 95 percent / Grubbs' catalyst 1'st generation / CH2Cl2 / 8 h / 20 °C View Scheme

tetrabutylammomium bromide; sodium hydroxide in water; 1,2-dichloro-ethane T=20°C; 112 h; Reflux;

sodium hydroxide; tetrabutylammomium bromide T=20°C; 8 h;