1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.42 h / -78 °C / |Inert atmosphere 1.2: 0.25 h / -78 °C / |Inert atmosphere 2.1: potassium fluoride / isopropyl alcohol / 8 h / 0 - 20 °C 3.1: 4-(N,N-dimethlyamino)pyridine / diethyl ether / 2 h / 25 °C / |Inert atmosphere 4.1: sodium tetrahydroborate / ethanol / 2 h / 0 °C / |Inert atmosphere 5.1: sodium nitrite; acetic acid / dimethyl sulfoxide / 20 h / 40 °C / |Inert atmosphere View Scheme

hydrogen; palladium on activated charcoal in methanol

1: 95 percent / Jones' reagent / acetone / 3 h / 0 °C 2: 35 percent / DCC / CH2Cl2 / 10 h / Ambient temperature 3: Jones' reagent View Scheme

1: 95 percent / Jones' reagent / acetone / 3 h / 0 °C 2: 35 percent / DCC / CH2Cl2 / 10 h / Ambient temperature 3: Jones' reagent View Scheme

jones' reagent in acetone T=0°C; 3 h;

1: MsCl; NaN3; TBAI / toluene / 6 h / 80 °C 2: 81 percent / PPh3; aq. HCl / tetrahydrofuran View Scheme