1: 98 percent / H2 / Rh/C / tetrahydrofuran / 18 h / 76000 Torr 2: 90 percent / pyridinium chlorochromate; Celite; sodium carbonate / CH2Cl2 / 4 h / 20 °C 3: 90 percent / p-toluenesulfonic acid monohydrate / toluene / 18 h / Heating 4: 95 percent / LiAlH4 / diethyl ether / 3 h / 20 °C 5: 97 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / 2 h / -60 - 20 °C View Scheme

1: Wittig reaction; 2: With borane-THF 3: With pyridinium chlorochromate Further stages.;

1: 90 percent / pyridinium chlorochromate; Celite; sodium carbonate / CH2Cl2 / 4 h / 20 °C 2: 90 percent / p-toluenesulfonic acid monohydrate / toluene / 18 h / Heating 3: 95 percent / LiAlH4 / diethyl ether / 3 h / 20 °C 4: 97 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / 2 h / -60 - 20 °C View Scheme

borane; pyridinium chlorochromate 1) THF, 0 deg C, 30 min, 2) CH2Cl2, reflux, 2 h; Yield given. Multistep reaction;

1.1: thionyl chloride / 70 °C 2.1: sodium acetate; pyridinium chlorochromate / dichloromethane / 7 h / 20 °C 3.1: toluene-4-sulfonic acid / toluene / |Reflux 4.1: lithium aluminium tetrahydride / tetrahydrofuran / |Reflux 4.2: 20 °C 5.1: dimethyl sulfoxide; oxalyl dichloride / dichloromethane / 0.58 h / -60 °C / |Inert atmosphere 5.2: -60 - 20 °C View Scheme

1: 1.) Na, 2.) H3O(1+), 3.) H(1+) / 1.) toluene, 3.) C6H6 2: 1.) H(1+), 2.) LiAlH4 / 1.) C6H6, 2.) THF, 3.) Collins, CH2Cl2 View Scheme

lithium aluminium tetrahydride; hydrogen cation 1.) C6H6, 2.) THF, 3.) Collins, CH2Cl2; Yield given. Multistep reaction;

1: 84 percent 2: 90 percent / Al2O3 / tetrahydrofuran / 10 h / 40 °C 3: 97 percent / diethyl ether / 0 °C 4: aq. H2SO4 / tetrahydrofuran / Heating View Scheme

1: 94 percent 2: 92 percent / Al2O3 / tetrahydrofuran / 10 h / 40 °C 3: 91 percent / diethyl ether / 0 °C 4: 97 percent / aq. H2SO4 / tetrahydrofuran / Heating 5: aq. AcOH, EtOH / 0 °C 6: 92 percent / POCl3, py / 1.) room temperature, 3 h, 2.) reflux, 10 min View Scheme