hydrogen; palladium on activated charcoal in methanol T=20°C; 24 h;

1: With pyridinium chlorochromate in dichloromethane T=20°C; 2 h; 2: With piperidinium acetate in benzene 2 h; Heating; Further stages.;

1: in tetrahydrofuran T=0 - 20°C; 2: in tetrahydrofuran; acetonitrile T=50°C; 23 h; Further stages.;

1.1: AgClO4 / Cp2ZrCl2 / CH2Cl2 / 4 h / 0 °C 1.2: 70 percent / aq. LiOH / tetrahydrofuran / 10 h / 20 °C 2.1: 88 percent / toluene; diethyl ether / 0.5 h / 20 °C 3.1: 60 percent / TiCl4 / CH2Cl2; diethyl ether / 0.25 h / -78 °C 4.1: PCC; 4A MS / CH2Cl2 / 2 h / 20 °C 4.2: 64 percent / piperidinium acetate / benzene / 2 h / Heating View Scheme

1.1: MsCl; Et3N / CH2Cl2 / 0.33 h / -10 °C 1.2: 82 percent / DBU / CH2Cl2 / 4 h / 20 °C 2.1: AgClO4 / Cp2ZrCl2 / CH2Cl2 / 4 h / 0 °C 2.2: 70 percent / aq. LiOH / tetrahydrofuran / 10 h / 20 °C 3.1: 88 percent / toluene; diethyl ether / 0.5 h / 20 °C 4.1: 60 percent / TiCl4 / CH2Cl2; diethyl ether / 0.25 h / -78 °C 5.1: PCC; 4A MS / CH2Cl2 / 2 h / 20 °C 5.2: 64 percent / piperidinium acetate / benzene / 2 h / Heating View Scheme

1.1: 57 percent / pTsOH / tetrahydrofuran; H2O / 4 h / Heating 2.1: MsCl; Et3N / CH2Cl2 / 0.33 h / -10 °C 2.2: 82 percent / DBU / CH2Cl2 / 4 h / 20 °C 3.1: AgClO4 / Cp2ZrCl2 / CH2Cl2 / 4 h / 0 °C 3.2: 70 percent / aq. LiOH / tetrahydrofuran / 10 h / 20 °C 4.1: 88 percent / toluene; diethyl ether / 0.5 h / 20 °C 5.1: 60 percent / TiCl4 / CH2Cl2; diethyl ether / 0.25 h / -78 °C 6.1: PCC; 4A MS / CH2Cl2 / 2 h / 20 °C 6.2: 64 percent / piperidinium acetate / benzene / 2 h / Heating View Scheme

1: 91 percent / imidazole / CH2Cl2 / 24 h / 20 °C 2: 96 percent / H2 / Pd/C / methanol / 24 h / 20 °C / atmospheric pressure View Scheme

diethyl ether

1.1: 88 percent / toluene; diethyl ether / 0.5 h / 20 °C 2.1: 60 percent / TiCl4 / CH2Cl2; diethyl ether / 0.25 h / -78 °C 3.1: PCC; 4A MS / CH2Cl2 / 2 h / 20 °C 3.2: 64 percent / piperidinium acetate / benzene / 2 h / Heating View Scheme

1.1: 60 percent / TiCl4 / CH2Cl2; diethyl ether / 0.25 h / -78 °C 2.1: PCC; 4A MS / CH2Cl2 / 2 h / 20 °C 2.2: 64 percent / piperidinium acetate / benzene / 2 h / Heating View Scheme