potassium fluoride T=300°C; 20 h;

in N,N-dimethyl-formamide

1: phosphorus pentachloride / 350 °C / Ni autoclave 2: potassium fluoride / 20 h / 300 °C View Scheme

in tetrahydrofuran T=-20°C;

1: 45 percent / diisobutylaluminum hydride / hexane; diethyl ether / 0 °C 2: 90 percent / NaBH4 / methanol / 0 °C 3: hydrazine / tetrahydrofuran / 50 °C 4: CuSO4; NaOH / ethanol / 30 °C 5: 78 percent / oxalyl chloride; DMSO / CH2Cl2 / -30 °C View Scheme

diisobutylaluminium hydride in diethyl ether; hexane T=0°C; Reduction;

in tetrahydrofuran T=-20°C;