manganese(IV) oxide in dichloromethane T=20°C; 2 h;

1.1: thionyl chloride / CH2Cl2; dimethylformamide / 2 h / 65 °C 1.2: 81.2 percent / CH2Cl2; dimethylformamide / 0 °C 2.1: Pd(PPh3)4 / toluene / 1 h / 20 °C 2.2: aq. Na2CO3 / toluene; ethanol / 8 h / 105 °C 2.3: 91 percent / HCl / diethyl ether / 20 °C 3.1: 85 percent / Ca(BH4)2 / ethanol / 2 h / 20 °C 4.1: 92 percent / MnO2 / CH2Cl2 / 2 h / 20 °C View Scheme

1.1: KH; t-BuLi / diethyl ether; hexane / 0.33 h / -78 °C 1.2: B(n-BuO)3 / diethyl ether; hexane / -78 - 20 °C 1.3: 88 percent / aq. H3PO4 / diethyl ether; hexane / 0 - 20 °C 2.1: Pd(PPh3)4 / toluene / 1 h / 20 °C 2.2: aq. Na2CO3 / toluene; ethanol / 8 h / 105 °C 2.3: 91 percent / HCl / diethyl ether / 20 °C 3.1: 85 percent / Ca(BH4)2 / ethanol / 2 h / 20 °C 4.1: 92 percent / MnO2 / CH2Cl2 / 2 h / 20 °C View Scheme

1.1: 99 percent / aq. Na2WO4; aq. H2O2 / 10 h / 80 - 85 °C 2.1: thionyl chloride / CH2Cl2; dimethylformamide / 2 h / 65 °C 2.2: 81.2 percent / CH2Cl2; dimethylformamide / 0 °C 3.1: Pd(PPh3)4 / toluene / 1 h / 20 °C 3.2: aq. Na2CO3 / toluene; ethanol / 8 h / 105 °C 3.3: 91 percent / HCl / diethyl ether / 20 °C 4.1: 85 percent / Ca(BH4)2 / ethanol / 2 h / 20 °C 5.1: 92 percent / MnO2 / CH2Cl2 / 2 h / 20 °C View Scheme

1.1: thallium(III) trifluoroacetate / trifluoroacetic acid / 2 h / 20 °C 1.2: 63 percent / CuBr2 / dimethylformamide / 1 h / 120 °C 2.1: 69.1 percent / aq. NaOH / methanol / 1.5 h / Heating 3.1: KH; t-BuLi / diethyl ether; hexane / 0.33 h / -78 °C 3.2: B(n-BuO)3 / diethyl ether; hexane / -78 - 20 °C 3.3: 88 percent / aq. H3PO4 / diethyl ether; hexane / 0 - 20 °C 4.1: Pd(PPh3)4 / toluene / 1 h / 20 °C 4.2: aq. Na2CO3 / toluene; ethanol / 8 h / 105 °C 4.3: 91 percent / HCl / diethyl ether / 20 °C 5.1: 85 percent / Ca(BH4)2 / ethanol / 2 h / 20 °C 6.1: 92 percent / MnO2 / CH2Cl2 / 2 h / 20 °C View Scheme

1.1: 69.1 percent / aq. NaOH / methanol / 1.5 h / Heating 2.1: KH; t-BuLi / diethyl ether; hexane / 0.33 h / -78 °C 2.2: B(n-BuO)3 / diethyl ether; hexane / -78 - 20 °C 2.3: 88 percent / aq. H3PO4 / diethyl ether; hexane / 0 - 20 °C 3.1: Pd(PPh3)4 / toluene / 1 h / 20 °C 3.2: aq. Na2CO3 / toluene; ethanol / 8 h / 105 °C 3.3: 91 percent / HCl / diethyl ether / 20 °C 4.1: 85 percent / Ca(BH4)2 / ethanol / 2 h / 20 °C 5.1: 92 percent / MnO2 / CH2Cl2 / 2 h / 20 °C View Scheme

1.1: Pd(PPh3)4 / toluene / 1 h / 20 °C 1.2: aq. Na2CO3 / toluene; ethanol / 8 h / 105 °C 1.3: 91 percent / HCl / diethyl ether / 20 °C 2.1: 85 percent / Ca(BH4)2 / ethanol / 2 h / 20 °C 3.1: 92 percent / MnO2 / CH2Cl2 / 2 h / 20 °C View Scheme

1.1: Pd(PPh3)4 / toluene / 1 h / 20 °C 1.2: aq. Na2CO3 / toluene; ethanol / 8 h / 105 °C 1.3: 91 percent / HCl / diethyl ether / 20 °C 2.1: 85 percent / Ca(BH4)2 / ethanol / 2 h / 20 °C 3.1: 92 percent / MnO2 / CH2Cl2 / 2 h / 20 °C View Scheme

1: 85 percent / Ca(BH4)2 / ethanol / 2 h / 20 °C 2: 92 percent / MnO2 / CH2Cl2 / 2 h / 20 °C View Scheme