lithium aluminium tetrahydride in diethyl ether 2 h; Heating;

1: 94 percent / 2,6-lutidine; TMSOTf / CH2Cl2 / 0.75 h / 20 °C 2: 83 percent / pyridine / 0.5 h / 20 °C 3: 83 percent / LiAlH4 / diethyl ether / 2 h / Heating View Scheme

1.1: 6.14 g / aq. NaHCO3 / acetone 2.1: NaH / dimethylformamide / 1 h / 20 °C 2.2: 85 percent / dimethylformamide / 24 h / 25 °C 3.1: 73 percent / ICl; NaN3 / acetonitrile; dimethylformamide / 70 h / Heating 4.1: 64 percent / toluene / 1 h 5.1: 94 percent / 2,6-lutidine; TMSOTf / CH2Cl2 / 0.75 h / 20 °C 6.1: 83 percent / pyridine / 0.5 h / 20 °C 7.1: 83 percent / LiAlH4 / diethyl ether / 2 h / Heating View Scheme

1.1: 1-chloroethyl chloroformate / 1,2-dichloro-ethane / 1 h / Heating 1.2: MeOH / 0.75 h / Heating 2.1: 6.14 g / aq. NaHCO3 / acetone 3.1: NaH / dimethylformamide / 1 h / 20 °C 3.2: 85 percent / dimethylformamide / 24 h / 25 °C 4.1: 73 percent / ICl; NaN3 / acetonitrile; dimethylformamide / 70 h / Heating 5.1: 64 percent / toluene / 1 h 6.1: 94 percent / 2,6-lutidine; TMSOTf / CH2Cl2 / 0.75 h / 20 °C 7.1: 83 percent / pyridine / 0.5 h / 20 °C 8.1: 83 percent / LiAlH4 / diethyl ether / 2 h / Heating View Scheme

1.1: NaH / dimethylformamide / 1 h / 20 °C 1.2: 85 percent / dimethylformamide / 24 h / 25 °C 2.1: 73 percent / ICl; NaN3 / acetonitrile; dimethylformamide / 70 h / Heating 3.1: 64 percent / toluene / 1 h 4.1: 94 percent / 2,6-lutidine; TMSOTf / CH2Cl2 / 0.75 h / 20 °C 5.1: 83 percent / pyridine / 0.5 h / 20 °C 6.1: 83 percent / LiAlH4 / diethyl ether / 2 h / Heating View Scheme

1: 73 percent / ICl; NaN3 / acetonitrile; dimethylformamide / 70 h / Heating 2: 64 percent / toluene / 1 h 3: 94 percent / 2,6-lutidine; TMSOTf / CH2Cl2 / 0.75 h / 20 °C 4: 83 percent / pyridine / 0.5 h / 20 °C 5: 83 percent / LiAlH4 / diethyl ether / 2 h / Heating View Scheme

1: 64 percent / toluene / 1 h 2: 94 percent / 2,6-lutidine; TMSOTf / CH2Cl2 / 0.75 h / 20 °C 3: 83 percent / pyridine / 0.5 h / 20 °C 4: 83 percent / LiAlH4 / diethyl ether / 2 h / Heating View Scheme

acetic acid

benzene