1.1: NaH; 15-crown-5 / dimethylformamide / 0.67 h / 20 °C 1.2: 69 percent / NaI / dimethylformamide / 10.5 h 2.1: 79 percent / aq. LiOH / methanol; tetrahydrofuran / 24 h / Heating 3.1: n-BuLi / hexane; tetrahydrofuran / 0.75 h / -78 - -70 °C 3.2: 21.5 g / hexane; tetrahydrofuran / 4.17 h / -78 - 20 °C 4.1: 17.9 g / HCl / 20 h / Heating 5.1: 12.2 g / aq. sodium periodate / methanol / 1 h / 0 °C 6.1: trifluoroacetic anhydride / 0.5 h / Heating 6.2: Et3N; MeOH 7.1: 0.90 g / Pd(PPh3)4; t-BuONa / Heating 8.1: 488 mg / aq. LiOH / methanol; tetrahydrofuran / 11 h / Heating 9.1: oxalyl chloride / CH2Cl2 / 0.83 h / 0 - 20 °C 10.1: 207 mg / aq. NH3 / 1 h View Scheme

potassium carbonate; tetrakis(triphenylphosphine) palladium(0) in toluene T=100°C; 23 h;

sodium amide in diethyl ether 4 h;