lithium aluminium tetrahydride in tetrahydrofuran 24 h; Heating;

sodium tetrahydroborate; boron trifluoride diethyl etherate in tetrahydrofuran 4 h; Heating;

1: 100 percent / DMAP / tetrahydrofuran / 6 h / Heating 2: 76 percent / LAH / tetrahydrofuran; diethyl ether / 24 h / Heating 3: 91 percent / tetrahydrofuran / -15 - 20 °C 4: 100 percent / aq. sodium metaperiodate / methanol / 24 h / Ambient temperature 5: 94 percent / Na2CO3 / toluene / 6 h / Heating 6: 79 percent / BBr3 / CH2Cl2 / 3.5 h / -78 - 20 °C View Scheme

Multi-step reaction with 2 steps 1: LiAlH4, H2SO4 (d= 1.86) / tetrahydrofuran / 24 h / Ambient temperature2: pyridine / 1 h / 60 °C  

Multi-step reaction with 5 steps 1: 100 percent / DMAP / tetrahydrofuran / 6 h / Heating2: 76 percent / LAH / tetrahydrofuran; diethyl ether / 24 h / Heating3: 91 percent / tetrahydrofuran / -15 - 20 °C4: 100 percent / aq. sodium metaperiodate / methanol / 24 h / Ambient temperature5: 94 percent / Na2CO3 / toluene / 6 h / Heating