pyridinium chlorochromate in dichloromethane 2 h; Heating;

1: 83.8 percent 2: 62 percent / pyridinium chlorochromate View Scheme

1: 1.) NaNH2 2.) EtONa / 1.) NH3 (liq.)-THF, -33 deg C, 3 h, 2.) NH3(liq.)-THF-EtOH, -78 deg C, 2 h 2: 97.7 percent / H2O / acetic acid / 16 h / Heating 3: 83.8 percent / tetrahydrofuran / 4 h / Ambient temperature 4: 62 percent / pyridinium chlorochromate / CH2Cl2 / 2 h / Heating View Scheme

1: 97.7 percent / H2O / acetic acid / 16 h / Heating 2: 83.8 percent / tetrahydrofuran / 4 h / Ambient temperature 3: 62 percent / pyridinium chlorochromate / CH2Cl2 / 2 h / Heating View Scheme