1: 55 percent / diethyl ether / 1) 0 deg C, 30 min, 2) 20-25 deg C, 4 h 2: 77 percent / pyridinium chlorochromate / CH2Cl2 / 6 h View Scheme

pyridinium chlorochromate

ammonium cerium(IV) nitrate in water; acetonitrile T=25°C; Yields of byproduct given;

hydrogenchloride in acetone T=20 - 23°C; 3 h;

1: tetrahydrofuran / 0 °C 2: PDC, HOAc, 4-A sieves / CH2Cl2 View Scheme

1: 71 percent / LiNH2, Fe(NO3)3 / tetrahydrofuran; liquid ammonia 2: 92 percent / H2, quinoline / Lindlar's catalyst / hexane; ethanol 3: 82 percent / Et3N / CH2Cl2 / 3 h 4: 2.) Li2CuCl4 / 1.) THF, 20 min, 2.) THF, a) -10 deg C, 3 h, b) RT, overnight 5: 78 percent / p-toluenesulphonic acid / methanol / 14 h / Ambient temperature 6: 66 percent / PCC / CH2Cl2 View Scheme

1: 92 percent / H2, quinoline / Lindlar's catalyst / hexane; ethanol 2: 82 percent / Et3N / CH2Cl2 / 3 h 3: 2.) Li2CuCl4 / 1.) THF, 20 min, 2.) THF, a) -10 deg C, 3 h, b) RT, overnight 4: 78 percent / p-toluenesulphonic acid / methanol / 14 h / Ambient temperature 5: 66 percent / PCC / CH2Cl2 View Scheme

1: 1) <(CH3)3Si>2NNa / 1) THF, reflux, 2 h, 2) -78 deg, 1 h, 3) room temperature, 10 h 2: 73 percent / 10percent aq. HCl / acetone / 3 h / 20 - 23 °C View Scheme

1: 63 percent / KOtBu / tetrahydrofuran / 1.) RT, 3 h; 2.) 50 deg C, 1 h 2: 88 percent / pyridinium chlorochromate View Scheme

2: (NH3)2Ce(NO3)6 / H2O; acetonitrile / 25 °C View Scheme