zinc in tetrahydrofuran Heating;

pyridine; chromium(VI) oxide in dichloromethane 1 h; Heating;

1: 82 percent / N-bromosuccinimide / CH2Cl2 / 1.) -20 deg C, 2 h, 2.) 15 deg C 2: 73 percent / 10 N aq. NaOH, NaBH4, chlorocobaloxime(III) / ethanol / 0.5 h / 50 - 60 °C 3: 60 percent / chromium trioxide, pyridine / CH2Cl2 / 1 h / Heating View Scheme

1.1: 93 percent / DMAP; pyridine / CH2Cl2 / 10 h / 20 °C 2.1: O3 / CH2Cl2 / -78 °C 2.2: 73 percent / Et2NH / CH2Cl2 / -78 - 20 °C 3.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / H2O; 2-methyl-propan-2-ol / 2.5 h / 20 °C 4.1: CH2Cl2; diethyl ether / 20 °C 5.1: 75 percent / AcCl / methanol / 7 h / 20 °C View Scheme

1.1: Mg / tetrahydrofuran / 2 h / Heating 1.2: 90 percent / tetrahydrofuran / 1 h / -78 °C 2.1: 93 percent / DMAP; pyridine / CH2Cl2 / 10 h / 20 °C 3.1: O3 / CH2Cl2 / -78 °C 3.2: 73 percent / Et2NH / CH2Cl2 / -78 - 20 °C 4.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / H2O; 2-methyl-propan-2-ol / 2.5 h / 20 °C 5.1: CH2Cl2; diethyl ether / 20 °C 6.1: 75 percent / AcCl / methanol / 7 h / 20 °C View Scheme

1.1: O3 / CH2Cl2 / -78 °C 1.2: 73 percent / Et2NH / CH2Cl2 / -78 - 20 °C 2.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / H2O; 2-methyl-propan-2-ol / 2.5 h / 20 °C 3.1: CH2Cl2; diethyl ether / 20 °C 4.1: 75 percent / AcCl / methanol / 7 h / 20 °C View Scheme

1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / H2O; 2-methyl-propan-2-ol / 2.5 h / 20 °C 2: CH2Cl2; diethyl ether / 20 °C 3: 75 percent / AcCl / methanol / 7 h / 20 °C View Scheme