pyridinium p-toluenesulfonate in dichloromethane T=20°C; Substitution; 23 h;

1: 1.) DMSO, oxalyl chloride, 2.) Et3N / 1.) CH2Cl2, -70 deg C, 40 min, 2.) CH2Cl2, from -70 deg C to -5 deg C, 2 h 2: 91 percent / benzene / 6.5 h / Heating 3: 97 percent / sodium borohydride, cerium(III) chloride heptahydrate / ethanol / 0.67 h 4: 95 percent / pyridine / Ambient temperature 5: 36 percent / KH2PO4, K2HPO4, water / acetone / 12 h / Ambient temperature; lipase PS "Amano" 6: 93 percent / HgCl2, CaCO3, water / acetonitrile / 7 h / Heating 7: benzene 8: benzene / 3 h / Heating 9: H2, AcOH / 10percent Pd/C / 18 h / 760 Torr / Ambient temperature 10: Et3N / tetrahydrofuran; benzene / 1 h / Ambient temperature 11: 91 percent / NaIO4, KMnO4, KH2PO4, K2HPO4 / H2O; acetone / 3 h / Ambient temperature 12: 80 percent / 4 N HCl in dioxane / 1 h / Ambient temperature View Scheme

boron trifluoride diethyl etherate in dichloromethane T=20°C; 5 h;

boron trifluoride diethyl etherate in chloroform 7 h; Ambient temperature;

boron trifluoride diethyl etherate

boron trichloride in dichloromethane

1: boron trifluoride etherate / CH2Cl2 / 0.67 h / Ambient temperature 2: methanol / 4 h / Ambient temperature View Scheme

methanol 4 h; Ambient temperature; Yield given;

1: 73 percent / (COCl)2; DMSO; Et3N / CH2Cl2 2: 64 percent / PPh3; t-BuOK / toluene / -20 °C View Scheme

N-ethyl-N,N-diisopropylamine in dichloromethane T=20°C; 15 h;