hydrogenchloride in tetrahydrofuran; water 4.5 h; Ambient temperature;

1: 91 percent / triethylamine / dimethylformamide / 24 h / Ambient temperature 2: 1.) LDA / 1.) THF, -78 deg C, 45 min, 2.) -78 deg C, 5 min 3: 60 percent / CrO3, pyridine / CH2Cl2 / 0.33 h / Ambient temperature 4: 60 percent / 5percent HCl / H2O; tetrahydrofuran / 4.5 h / Ambient temperature View Scheme

dihydrogen peroxide in tetrahydrofuran 1.) 0 deg C, 30 min, 2.) room temperature, 30 min;

1: 64 percent / sodium hydride, DMSO / 1.5 h / 80 °C 2: 1.) LDA / 1.) THF, -78 deg C, 45 min, 2.) -78 deg C -> room temperature, 30 min 3: 577 mg / 30percent H2O2 / tetrahydrofuran / 1.) 0 deg C, 30 min, 2.) room temperature, 30 min View Scheme

1: 60 percent / CrO3, pyridine / CH2Cl2 / 0.33 h / Ambient temperature 2: 60 percent / 5percent HCl / H2O; tetrahydrofuran / 4.5 h / Ambient temperature View Scheme

1: 1.) LDA / 1.) THF, -78 deg C, 45 min, 2.) -78 deg C -> room temperature, 30 min 2: 577 mg / 30percent H2O2 / tetrahydrofuran / 1.) 0 deg C, 30 min, 2.) room temperature, 30 min View Scheme

1.1: 55 percent / sodium hypochlorite; triethylamine / H2O; CHCl3 / 0 - 4 °C 2.1: hydrogen / Pd/C / methanol / 10 h 2.2: 72 percent / aqueous hydrochloric acid / H2O / 3 h 3.1: lithium diisopropylamide / tetrahydrofuran; heptane; ethylbenzene / 0.5 h / -78 °C 3.2: 70 percent / tetrahydrofuran; heptane; ethylbenzene / 3 h / -78 °C 4.1: triethylamine; methanesulfonyl chloride / tetrahydrofuran / 1.5 h / 0 °C View Scheme

1.1: hydrogen / Pd/C / methanol / 10 h 1.2: 72 percent / aqueous hydrochloric acid / H2O / 3 h 2.1: lithium diisopropylamide / tetrahydrofuran; heptane; ethylbenzene / 0.5 h / -78 °C 2.2: 70 percent / tetrahydrofuran; heptane; ethylbenzene / 3 h / -78 °C 3.1: triethylamine; methanesulfonyl chloride / tetrahydrofuran / 1.5 h / 0 °C View Scheme

1.1: lithium diisopropylamide / tetrahydrofuran; heptane; ethylbenzene / 0.5 h / -78 °C 1.2: 70 percent / tetrahydrofuran; heptane; ethylbenzene / 3 h / -78 °C 2.1: triethylamine; methanesulfonyl chloride / tetrahydrofuran / 1.5 h / 0 °C View Scheme