sodium carbonate in diethyl ether T=20°C; 6 h;

1: PhNEt2 / toluene / Heating 2: 67 percent / Bu3SnH, azo(cyclohexanecarbonitrile) / toluene / Heating 3: MCPBA / CH2Cl2 / -30 °C 4: TFAA / CH2Cl2 / 72 h / Ambient temperature 5: 70 percent / Bu3SnH, azo(cyclohexanecarbonitrile) / toluene / Heating 6: 52 percent / BH3*THF / tetrahydrofuran / 1.) r.t., 15 min, 2.) reflux, 1.5 h View Scheme

1.1: 71 percent / aq. Na2CO3 / diethyl ether / 2 h / 23 - 27 °C 2.1: POCl3 / acetonitrile / 2 h / 80 - 83 °C 2.2: 8 percent / NaBH4 / methanol / 2 h / -78 °C View Scheme

1: AlCl3 / CH2Cl2 / 3 h / Heating 2: 10 percent / 4 h / 185 - 190 °C View Scheme

hydrogenchloride; tin(IV) chloride 1.) CH2Cl2, RT, 2 h, 2.) RT, 16 h; Yield given. Multistep reaction;

1: 6.38 g / aq. Na2CO3 / diethyl ether / 6 h / 20 °C 2: 76 percent / POCl3 / acetonitrile / 4 h / Heating View Scheme