IRN-77 Amberlite in acetone 24 h; Ambient temperature;

1: 90 percent / paratoluenesulfonic acid / toluene / 15 h / Heating 2: 95 percent / K2CO3 / methanol / 3 h / Heating 3: N,N-dimethylaminopyridine, triethylamine / CH2Cl2 / 60 h / Ambient temperature 4: 94 percent / DIBAL-H / toluene / 4 h / Ambient temperature 5: 1.) butyllithium / 1.) THF, hexane, 1.5 h, 20 deg C: 2.) THF, 66 deg C, 12 h 6: 262 mg / tetrabutylammonium fluoride / tetrahydrofuran / 20 °C 7: 1.) N-methyl piperidone; 2.) aluminium isopropoxide / 1.) toluene, boiling; 2.) toluene, 110 deg C, 5 h 8: 59 percent / IRN-77 Amberlite / acetone / 24 h / Ambient temperature View Scheme

1: 1.) butyllithium / 1.) THF, hexane, 1.5 h, 20 deg C: 2.) THF, 66 deg C, 12 h 2: 262 mg / tetrabutylammonium fluoride / tetrahydrofuran / 20 °C 3: 1.) N-methyl piperidone; 2.) aluminium isopropoxide / 1.) toluene, boiling; 2.) toluene, 110 deg C, 5 h 4: 59 percent / IRN-77 Amberlite / acetone / 24 h / Ambient temperature View Scheme