1: 96.7 percent / NaH / tetrahydrofuran / -30 deg C to RT, reflux 2: 72 percent / H2 / 10 percent Pd/C / ethanol / Ambient temperature 3: t-BuONO / tetrahydrofuran / Heating 4: LiAlH4 / tetrahydrofuran / Heating View Scheme

1: 72 percent / H2 / 10 percent Pd/C / ethanol / Ambient temperature 2: t-BuONO / tetrahydrofuran / Heating 3: LiAlH4 / tetrahydrofuran / Heating View Scheme

1: 94 percent / diethyl ether / 2 h / Heating 2: 96.7 percent / NaH / tetrahydrofuran / -30 deg C to RT, reflux 3: 72 percent / H2 / 10 percent Pd/C / ethanol / Ambient temperature 4: t-BuONO / tetrahydrofuran / Heating 5: LiAlH4 / tetrahydrofuran / Heating View Scheme

1: thionylchloride / -30 deg C to Rt, reflux, 1 h 2: triethylamine / ethanol / 4 h / Heating 3: 94 percent / diethyl ether / 2 h / Heating 4: 96.7 percent / NaH / tetrahydrofuran / -30 deg C to RT, reflux 5: 72 percent / H2 / 10 percent Pd/C / ethanol / Ambient temperature 6: t-BuONO / tetrahydrofuran / Heating 7: LiAlH4 / tetrahydrofuran / Heating View Scheme

1: triethylamine / ethanol / 4 h / Heating 2: 94 percent / diethyl ether / 2 h / Heating 3: 96.7 percent / NaH / tetrahydrofuran / -30 deg C to RT, reflux 4: 72 percent / H2 / 10 percent Pd/C / ethanol / Ambient temperature 5: t-BuONO / tetrahydrofuran / Heating 6: LiAlH4 / tetrahydrofuran / Heating View Scheme

lithium aluminium tetrahydride in tetrahydrofuran Heating; Yield given;

1: t-BuONO / tetrahydrofuran / Heating 2: LiAlH4 / tetrahydrofuran / Heating View Scheme