N-ethyl-N,N-diisopropylamine in dichloromethane T=20°C; 28 h;

phthalic anhydride; hydroxylamine hydrochloride; triethylamine in acetonitrile 8 h; Heating;

carbon tetrabromide in isopropyl alcohol 1.5 h; Heating;

Jone's reagent in acetone T=0°C; Jones oxidation;

1: NaH / tetrahydrofuran / Ambient temperature 2: LiOH / H2O / Ambient temperature 3: 90 percent / diphenyl phosphorazidate, Et3N / toluene / 110 °C 4: 1.) NaH / 1.) THF, 0 deg C, 2.) Ph2O, 250 deg C, 3 min 5: 85 percent / NaI, chlorotrimethylsilane / acetonitrile / -20 °C 6: 1.) TMS2NH, chlorotriomethylsilane, 2.) MoO5*pyridine*HMPA / 1.) reflux, 2.) CH2Cl2, room temp. View Scheme