1.1: sodium tetrahydroborate / methanol; water / 0.25 h / -15 °C / |Inert atmosphere 2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.42 h / -78 °C / |Inert atmosphere 2.2: 0.25 h / -78 °C / |Inert atmosphere 3.1: potassium fluoride / isopropyl alcohol / 8 h / 0 - 20 °C 4.1: 4-(N,N-dimethlyamino)pyridine / diethyl ether / 2 h / 25 °C / |Inert atmosphere 5.1: sodium tetrahydroborate / ethanol / 2 h / 0 °C / |Inert atmosphere 6.1: sodium nitrite; acetic acid / dimethyl sulfoxide / 20 h / 40 °C / |Inert atmosphere View Scheme

methanol; sodium tetrahydroborate T=0°C; 0.333333 h; Yield given;

methanol; sodium tetrahydroborate T=0°C; 0.333333 h; Yield given;

in tetrahydrofuran; diethyl ether 3 h; Ambient temperature; Yield given;