pyridinium chlorochromate in dichloromethane 4 h; Ambient temperature;

1: 53 percent / NaH / tetrahydrofuran; dimethylformamide / 4 h / 20 °C 2: 78 percent / Pr4NRuO4; NMO; MS4A / acetonitrile View Scheme

1: 1.) Na / 1.) xylene, 130 deg C, 2.) xylene, reflux, 15 min 2: 81 percent / oxalyl chloride, DMSO / CH2Cl2 / 1.5 h / -78 °C View Scheme

1: 53 percent / NaH / tetrahydrofuran; dimethylformamide / 4 h / 20 °C 2: 78 percent / Pr4NRuO4; NMO; MS4A / acetonitrile View Scheme

in dichloromethane T=0°C; 0.5 h;

oxalyl dichloride; sodium hydride; dimethyl sulfoxide 1.) THF, 60 deg C; 2.) CH2Cl2, r.t.; Yield given. Multistep reaction;

1: 92 percent / n-BuLi / tetrahydrofuran / 1 h / 20 °C 2: H2 / 5 percent Pd/C / ethyl acetate / 3 h / 20 °C 3: 90 percent / PCC / CH2Cl2 / 2 h / 20 °C 4: 86 percent / NaH / tetrahydrofuran / 4 h / 0 - 20 °C View Scheme

1: 83 percent / tetrahydrofuran / 0 °C 2: 89 percent / (COCl)2, DMSO / CH2Cl2 / Ambient temperature 3: 90 percent / FeCl3 / CH2Cl2 / Ambient temperature 4: 92 percent / p-TsOH 5: (COCl)2, DMSO / CH2Cl2 / Ambient temperature 6: KN(SiMe3)2 / tetrahydrofuran / 0 °C 7: 1.) PhSSPh; 2.) BF3*Et2O / 1.) irrad.,r.t., hexane; 2.) CH2Cl2, r.t. 8: 1N NaOH / methanol 9: SOCl2 / benzene / Heating 10: 70 percent / LiN(SiMe3)2 / tetrahydrofuran / -100 °C 11: 97 percent / NaBH4 / methanol / 0 °C 12: NCS, AgNO3 13: 10percent MeOH, CF3COOH / 60 °C 14: 68 percent / 2N NaOH / methanol / Ambient temperature 15: H2 / 10percent Pd/C / methanol View Scheme

1: 92 percent / n-BuLi / tetrahydrofuran / 1 h / 20 °C 2: H2 / 5 percent Pd/C / ethyl acetate / 3 h / 20 °C 3: 90 percent / PCC / CH2Cl2 / 2 h / 20 °C View Scheme