1: 1.) borane*THF komplex, 2.) 3 N aq. KOH, 30 percent H2O2 / 1.) THF, 0 deg C, 2 h, 2.) H2O, 0 deg C, 2 h 2: 1.09 g / oxalyl chloride, dimethyl sulfoxide / CH2Cl2 / 0.25 h / -60 °C 3: 89 percent / K2CO3 / methanol / 12 h / 0 °C 4: 98 percent / NaBH4 / ethanol / 0.5 h / 0 °C 5: 99 percent / pyridine / 13 h / Ambient temperature 6: LiAlH4 / tetrahydrofuran / 2 h / Heating 7: 10 percent aq. HCl / tetrahydrofuran / 8 h / Ambient temperature 8: 96 percent / 1.) 1.2 M butyl lithium, diisopropylamine / hexane; tetrahydrofuran / 0.25 h / -78 °C 9: 1.) ozone, 2.) dimethyl sulfide / 1.) MeOH/CH2Cl2, -78 deg C, 2.) -78 deg C, 0.5 h; r. t., 3 h 10: p-TsOH*H2O / cyclohexane / 6 h / Heating View Scheme

Multi-step reaction with 2 steps 1: 77 percent / KHSO4 / cyclohexane / 6 h / Heating2: 92 percent / PPTS / benzene / 25 h / Heating  

With  potassium hydroxide; borane-THF; dihydrogen peroxide  1.) THF, 0 deg C, 2 h, 2.) H2O, 0 deg C, 2 h;  Yield given. Multistep reaction;   

Multi-step reaction with 2 steps 1: 1.) borane*THF komplex, 2.) 3 N aq. KOH, 30 percent H2O2 / 1.) THF, 0 deg C, 2 h, 2.) H2O, 0 deg C, 2 h2: 1.09 g / oxalyl chloride, dimethyl sulfoxide / CH2Cl2 / 0.25 h / -60 °C  

Multi-step reaction with 5 steps 1: 1.) borane*THF komplex, 2.) 3 N aq. KOH, 30 percent H2O2 / 1.) THF, 0 deg C, 2 h, 2.) H2O, 0 deg C, 2 h2: 1.09 g / oxalyl chloride, dimethyl sulfoxide / CH2Cl2 / 0.25 h / -60 °C3: 89 percent / K2CO3 / methanol / 12 h / 0 °C4: 98 percent / NaBH4 / ethanol / 0.5 h / 0 °C5: 99 percent / pyridine / 13 h / Ambient temperature  

Multi-step reaction with 3 steps 1: 1.) borane*THF komplex, 2.) 3 N aq. KOH, 30 percent H2O2 / 1.) THF, 0 deg C, 2 h, 2.) H2O, 0 deg C, 2 h2: 1.09 g / oxalyl chloride, dimethyl sulfoxide / CH2Cl2 / 0.25 h / -60 °C3: 89 percent / K2CO3 / methanol / 12 h / 0 °C  

Multi-step reaction with 4 steps 1: 1.) borane*THF komplex, 2.) 3 N aq. KOH, 30 percent H2O2 / 1.) THF, 0 deg C, 2 h, 2.) H2O, 0 deg C, 2 h2: 1.09 g / oxalyl chloride, dimethyl sulfoxide / CH2Cl2 / 0.25 h / -60 °C3: 89 percent / K2CO3 / methanol / 12 h / 0 °C4: 98 percent / NaBH4 / ethanol / 0.5 h / 0 °C  

Multi-step reaction with 7 steps 1: 1.) borane*THF komplex, 2.) 3 N aq. KOH, 30 percent H2O2 / 1.) THF, 0 deg C, 2 h, 2.) H2O, 0 deg C, 2 h2: 1.09 g / oxalyl chloride, dimethyl sulfoxide / CH2Cl2 / 0.25 h / -60 °C3: 89 percent / K2CO3 / methanol / 12 h / 0 °C4: 98 percent / NaBH4 / ethanol / 0.5 h / 0 °C5: 99 percent / pyridine / 13 h / Ambient temperature6: LiAlH4 / tetrahydrofuran / 2 h / Heating7: 10 percent aq. HCl / tetrahydrofuran / 8 h / Ambient temperature  

Multi-step reaction with 8 steps 1: 1.) borane*THF komplex, 2.) 3 N aq. KOH, 30 percent H2O2 / 1.) THF, 0 deg C, 2 h, 2.) H2O, 0 deg C, 2 h2: 1.09 g / oxalyl chloride, dimethyl sulfoxide / CH2Cl2 / 0.25 h / -60 °C3: 89 percent / K2CO3 / methanol / 12 h / 0 °C4: 98 percent / NaBH4 / ethanol / 0.5 h / 0 °C5: 99 percent / pyridine / 13 h / Ambient temperature6: LiAlH4 / tetrahydrofuran / 2 h / Heating7: 10 percent aq. HCl / tetrahydrofuran / 8 h / Ambient temperature8: 96 percent / 1.) 1.2 M butyl lithium, diisopropylamine / hexane; tetrahydrofuran / 0.25 h / -78 °C