sodium hydroxide in 1,4-dioxane; water

triethylsilane; boron trifluoride diethyl etherate in dichloromethane T=-78°C; 2 h;

1: With ozone in methanol; dichloromethane T=-78°C; 0.266667 h; 2: With dimethylsulfide in methanol; dichloromethane T=-78 - 23°C; 20 h; 3: With triethylsilane; boron trifluoride diethyl etherate in dichloromethane T=-78°C; 2.5 h; Further stages.;

1: 52 percent / acetonitrile / 4 h / Ambient temperature 2: 97 percent / aq. NaHCO3 / acetone / 2 h / Ambient temperature 3: 1.) O3, 2.) Me2S / 1) CH2Cl2, MeOH, dry ice/acetone bath, 6 psi O2; 2) CH2Cl2, CH3OH, cooling --> rt, 20 h 4: 80 percent / Et3SiH, boron trifluoride diethyl etherate / CH2Cl2 / 2 h / -78 °C View Scheme

1: 97 percent / aq. NaHCO3 / acetone / 2 h / Ambient temperature 2: 1.) O3, 2.) Me2S / 1) CH2Cl2, MeOH, dry ice/acetone bath, 6 psi O2; 2) CH2Cl2, CH3OH, cooling --> rt, 20 h 3: 80 percent / Et3SiH, boron trifluoride diethyl etherate / CH2Cl2 / 2 h / -78 °C View Scheme

1: 97 percent / aq. NaHCO3 / acetone / 2 h / Ambient temperature 2: 1.) O3, 2.) Me2S / 1) CH2Cl2, MeOH, dry ice/acetone bath, 6 psi O2; 2) CH2Cl2, CH3OH, cooling --> rt, 20 h 3: 80 percent / Et3SiH, boron trifluoride diethyl etherate / CH2Cl2 / 2 h / -78 °C View Scheme

methanol; sodium hydroxide in tetrahydrofuran

hydrogen in methanol; dichloromethane