N-bromosuccinmide; 2,2'-azo-bisisobutyronitrile; dibenzoyl peroxide in tetrachloromethane 1.5 h; Heating; Product distribution;

1: LiAlH4 / diethyl ether / -45 - -40 °C 2: 4 h / Heating View Scheme

1.1: ammonium hydroxide / water / 2 h / 70 °C 2.1: Lawesson's reagent / toluene / 2 h / Reflux 3.1: ethanol / 2 h / Reflux 4.1: selenium(IV) oxide / acetic acid / 12 h / Reflux 5.1: tetrahydrofuran / 0.5 h / 20 °C 6.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C 7.1: ammonium acetate / 12 h / Reflux 8.1: potassium carbonate / ethanol; dichloromethane 9.1: 1H-imidazole / N,N-dimethyl-formamide / 24 h / 20 °C 10.1: lithium hydroxide hydrate / tetrahydrofuran; water / 2 h 11.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 3 h / Inert atmosphere 12.1: BOP-Cl; triethylamine / acetonitrile / 3 h 13.1: triethylamine / dichloromethane / 1 h / 20 °C / Inert atmosphere 14.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1 h / Inert atmosphere 15.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h 16.1: Dess-Martin periodane / dichloromethane / 2 h 17.1: sodium dihydrogenphosphate; sodium chlorite; 2-methyl-but-2-ene / tetrahydrofuran; water / 2 h 17.2: pH 2 18.1: BOP-Cl; triethylamine / acetonitrile / Inert atmosphere 19.1: lithium hydroxide hydrate / tetrahydrofuran; water / 2 h / 20 °C 19.2: pH 3 20.1: dichloromethane / 2 h / 20 °C 21.1: diphenyl phosphoryl azide / N,N-dimethyl-formamide / 2 h / 20 °C View Scheme

1: 84 percent / LiAlH4 / diethyl ether / 3 h / -78 °C 2: 85 percent / Ph3P; CBr4 / CCl4 / 3 h / 20 °C 3: 86 percent / 3 h / 160 °C View Scheme